Water → N-(2-Amino-5-nitropyridin-3-yl)-4-nitrobenzamide

HRID 854076Notes

Reaction equation

HRID 854076 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13].O>N1C=CC=CC=1>[NH2:1][C:2]1[C:7]([NH:8][C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:23][CH:22]=2)=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 85024-Nitrobenzoyl chlorideHCID 34801515-Nitropyridine-2,3-diamine

Product 1

HCID 58932933N-(2-Amino-5-nitropyridin-3-yl)-4-nitrobenzamideYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2,3-Diamino-5-nitropyridine (3) in dry pyridine (85 mL) was added 4-nitrobenzoylchloride (0.875 g, 4.7 mmol) and the mixture was stirred at room temperature for 20 h. The mixture was then poured into H2O (250 mL) and stirred for 30 minutes. The resulting yellow solid was collected by filtration and rinsed with H2O until no pyridine remained. The solid was dried in vacuuo at 80 C to give 6 as a yellow solid (1.15 g, 3.8 mmol, 81%). 1H NMR (500 MHz, DMSO-d6) δ10.12 (br s, 1H), 8.83 (d, J=2.55 Hz, 1H), 8.84 (d, J=8.5 Hz, 2H), 8.35 (d, J=2.45 Hz, 2H), 8.24 (d, J=8.7 Hz, 2H), 7.62 (br s, 2H). EIMS M−1 302.3.

Workup

  1. stirringstirred for 30 minutes
  2. filtrationThe resulting yellow solid was collected by filtration
  3. washrinsed with H2O until no pyridine
  4. customThe solid was dried in vacuuo at 80 C

Sources & evidence

ORD record
ord-54fd63118593484c84c0b78d66da8d5d
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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