Water → Methyl 2-[(4-amino-3-nitrophenyl)carbonyl]benzoate

HRID 2261967Notes

Reaction equation

HRID 2261967 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[O:9])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[C:22](=O)([O-])[O-].[Cs+].[Cs+].IC.O>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([O:14][CH3:22])=[O:13])=[O:9])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 27975222-(4-Amino-3-nitrobenzoyl)benzoic acid

Product 1

HCID 14994663Methyl 2-[(4-amino-3-nitrophenyl)carbonyl]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[(4-amino-3-nitrophenyl)carbonyl]benzoic acid (10 g, 35 mmol) in DMF (50 mL) was treated with cesium carbonate (23 g, 70 mmol) followed by iodomethane (2.2 mL, 35 mmol). The mixture was stirred at rt for 1 h, after which time 50 mL of water was added. A yellow precipitate formed. The solid was collected by filtration, rinsed with water, and dried in vacuo. Desired methyl 2-[(4-amino-3-nitrophenyl)carbonyl]benzoate was obtained as a yellow solid (8.36 g, 27.8 mmol, 80% yield). 1H NMR (400 MHz, d6-DMSO): 8.12 (br s, 2H), 8.10 (d, 1H), 7.78-7.75 (m, 2H), 7.70 (m, 1H), 7.48 (dd, 1H), 7.10 (d, 1H), 3.64 (s, 3H); MS (EI) for C15H12N2O5: 323 (MNa+).

Workup

  1. customA yellow precipitate formed
  2. filtrationThe solid was collected by filtration
  3. washrinsed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7fc179b902a543bd8de7ffce7c113cc7
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

Loading…