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

HRID 2367121Notes

Reaction equation

HRID 2367121 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-0ba018c9dfd1464eabb076f08dccc258
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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