Synthesis and properties of new 6,7-dimethoxy-3,4-dihydroand 1,2,3,4-tetrahydroisoquinolines. II. 1-Phenyl- and 1-benzyl- derivatives was written by Viel, Claude;Dorme, Regina;Rumpf, Paul. And the article was included in Bulletin de la Societe Chimique de France in 1966.Application In Synthesis of 2-(2-Chlorophenyl)acetamide This article mentions the following:
Pharmacol. active papaverine analogs were prepd, o-ClC6H4CH2Cl (100 g.), 50 g. KCN in 100 cc. H2O, and 1l. EtOH was refluxed 7 hrs., the EtOH stripped and residue poured into 2 1. ice-H2O to give 49 g. o-ClC6H4CH2CN, b24 133-43°. The nitrile was hydrolyzed to o-ClC6H4CONH2, m. 174°, and finally to o-ClC6H4CO2H, m. 95°. Also prepared was o-FC6H4CO2H (I), m. 59°. BzH was nitrated to give m-NO2C6H4CHO (II), b4 114-23°, and 97 g. aldehyde was reduced with 95 g. KBH4 in MeOH to give m-NO2C6H4CH2OH (III), b1.5 140-2°. Prepared from III was m-NO2C6H4CH2Cl, m. 45-7° and from the chloride, m-NO2C6H4CH2CN, b0.5 145-50°. mClC6H4COCl (76 g.) was reduced by the Rosenmund reaction to give 10 g. m-ClC6H4CHO (IV), b23 110-12°. II was reduced and the resulting m-NH2C6H4CHO treated in situ by the Sandmeyer reaction to give IV. IV was condensed with hippuric acida zlactone to give 2-phenyl-4-(3-chlorobenzylidene)-5-oxazolone (V), m. 164°. V was refluxed with 10% NaOH and the resulting product treated with 130-volume H2O2 2 hrs. to give 3 g. methyl 3 nitrophenylacetate, b20 125-30°. Similarly prepared were pClC6H4CH2CN, b. 264-7°, and p-ClC6H4CH2CO2H, m. 106°. 3,4-Dimethoxy-β-phenethylamine, b22 170° (picrate, m. 164.5-5.0°) and β-phenethylamine (VI), b15 93° (picrate m. 174°) were also prepared A mixture of 7.7 g. I and 6 g. VI was heated 3 hrs. at 180° to give 8.82 g. β-phenethyl-o-fluorophenylacetamide (VII), m. 102-3°. Similarly prepared were homoveratryl-o-chlorobenzamide, b1 180-5°, m. 90° homoveratryl-o-chlorophenylacetamide, m. 120° and homoveratryl-m-chlorophenylacetamide, m. 92°. VII (2.58 g.) in PhMe was cyclized by refluxing with 15 cc. POCl3 1.5 hrs. to give 3,4-dihydro-1-(o-fluorobenzyl)isoquinoline (VIII), m. 156-7°. Polyphosphoric acid was also used for cyclization. Similarly prepared were 3,4dihydro-1-(o-chlorobenzyl)isoquinoline, m. 148°; 6,7-dimethoxy 3,4-dihydro-1-(o-chlorophenyl)isoquinoline (HBr salt, m. 192°, picrate, m. 182°) and 6,7-dimethoxy-3,4-dihydro-1-(o-fluorobenzyl)isoquinoline; HBr salt m. 190° picrate m. 185°. VIII (530 mg.) in MeOH was reduced with 500 mg. NaBH4 in aqueous MeOH to give 1,2,3,4-tetrahydro-1-(o-fluorobenzyl)isoquinoline, m. 192.5°. Similarly prepared were 6,7-dimethoxy-1,2,3,4-tetrahydro-1-(p-nitrophenyl)isoquinoline (HCl salts, m. 260°, picrate, m. 160°) and 6,7-dimethoxy-1,2,3,4-tetrahydro-1-(p-nitrobenzyl)isoquinoline; tartrate salt m. 132°. p-Chlorobenzylidenehomoveratrylamine (15 g.) was refluxed 1 hr. at 100° with 67 cc. 24% HCl to give 10 g. 6,7-dimethoxy-1,2,3,4-tetrahydro-1-(p-chlorophenyl)isoquinoline; HCl salt m. 230°. In the experiment, the researchers used many compounds, for example, 2-(2-Chlorophenyl)acetamide (cas: 10268-06-1Application In Synthesis of 2-(2-Chlorophenyl)acetamide).
2-(2-Chlorophenyl)acetamide (cas: 10268-06-1) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Application In Synthesis of 2-(2-Chlorophenyl)acetamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics