Water → N-(4-nitropyridin-2-yl)acetamide

HRID 1640107Notes

Reaction equation

HRID 1640107 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12].O>N1C=CC=CC=1>[N+:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:11](=[O:13])[CH3:12])[CH:7]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 27628222-Amino-4-nitropyridine

Product 1

HCID 57495175N-(4-nitropyridin-2-yl)acetamideYield 101.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-4-nitropyridine (3.0 g, 0.018 mol) in pyridine (40 mL) was added acetic anhydride (5.2 mL 0.055 mol). The reaction mixture was allowed to stir for 30 h at rt. Water was added to the solution and the resulting solid was collected and washed with water and dried under vacuum to give N-(4-nitropyridin-2-yl)acetamide as a brown solid (3.3 g, 99%). 1HNMR (300 MHz, CDCl3) δ: 8.90 (s, 1H), 8.50 (d, 1H), 8.30 (br s, 1H), 7.8 (dd, 1H), 2.3 (s, 3H); LCMS: (FA) ES+ 182.2.

Workup

  1. customthe resulting solid was collected
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-17e4f08afce84eb2acc63fab1911f010
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

Loading…