Ammonia → HCID 54209758, compound

HRID 1449378Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([NH2:11])=[O:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[NH3:16]>>[NH2:16][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([NH2:11])=[O:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Participants

Reactant 2

HCID 222Ammonia

HCID 54127339HCID 54127339, compound

Product 1

HCID 54209758HCID 54209758, compound

Procedure

By an original process, 2-(4'-chloro-3'-nitro-phenyl) propionamide (I), thus obtained, is treated with ammonia in an alcohol solution to furnish 2-(4'-amino-3'-nitro-phenyl) propionamide (II) which, when hydrolyzed in an acid medium, is transformed into 2-(4'-amino-3'-nitro-phenyl) propionic acid (III). This, when treated with 2,5-dimethoxytetrahydrofuran (a mixture of cis/trans isomers) produces 2-(3'-nitro-4'-[1"-pyrrolyl] phenyl) propionic acid (A). Catalytic hydrogenation of the latter in the presence of palladium on activated charcoal produces 2-(3'-amino-4'-[1"-pyrrolyl] phenyl) propionic acid (B).

Sources & evidence

ORD record: ord-fce7f7594904482ba64caf591b319451
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04190665

Reaction notes

Loading…