Water → 6-Amino-5-(4-nitro-benzoylamino)-nicotinic acid methyl ester

HRID 854096Notes

Reaction equation

HRID 854096 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:11])=[N:6][CH:5]=1.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].O>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([NH:10][C:20](=[O:21])[C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=2)[C:7]([NH2:11])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 85024-Nitrobenzoyl chlorideHCID 9920476Methyl 5,6-diaminopyridine-3-carboxylate

Product 1

HCID 589329236-Amino-5-(4-nitro-benzoylamino)-nicotinic acid methyl esterYield 68.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5,6-Diamino-nicotinic acid methyl ester (4) (3.22 g, 19 mmol) in dry pyridine (100 ml) was added 4-nitrobenzoyl chloride (3.5 g, 19 mmol) and the mixture stirred for 18 h. The mixture was poured into H2O and the resulting solid collected by filtration, dried in vacuo to give the product as a yellow solid (4.05 g, 13 mmol, 66%). 1H NMR (500 MHz, DMSO-d6) δ9.98 (s, 1H), 8.47 (s, 1H), 8.36 (d, J=8.7 Hz, 2H), 8.23 (d, J=8.7 Hz, 2H), 8.0 (s, 1H), 6.92 (s, 2H), 3.79 (s, 3H), EIMS m/z M−1 315.4.

Workup

  1. filtrationthe resulting solid collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-d86aeedf9ca54b8d82c13aae95873693
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

Loading…