(4-Amino-3-nitrophenyl)-2-pyridinylmethanone → HCID 21432586, compound

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[NH2:18])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8])([O-])=O.[H][H]>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[NH2:18])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8]

Participants

Procedure

A suspension of 20 g. (0.082 mol) of 2-(3-nitro-4-aminobenzoyl)pyridine in 1 liter of tetrahydrofuran containing 5 g. of 5% palladium on carbon was reduced with hydrogen under a pressure of 3 atmospheres. The resulting mixture was filtered and concentrated in vacuo to a reddish oil which was dissolved in a minimum amount of methylene chloride and diluted with petroleum ether to yield 2-(3,4-diaminobenzoyl)pyridine as a slightly unstable yellow solid, mp. 137° -138° C. (water).