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

HRID 2262003Notes

Reaction equation

HRID 2262003 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].S(=O)(=O)(O)O.[CH3:27]O>>[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][CH3:27])=[O:13])=[O:9])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27975222-(4-Amino-3-nitrobenzoyl)benzoic acid

Product 1

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

Procedure

A solution of 2-[(4-amino-3-nitrophenyl)carbonyl]benzoic acid (4.60 g, 16.00 mmol) in methanol (300 mL) in the presence of catalytic amount of cc. sulfuric acid was heated to reflux for 18 h. The solution was cooled to room temperature and the solvent was evaporated. The yellow precipitate formed was collected by filtration, washed with water and dried in vacuo to provide methyl 2-[(4-amino-3-nitrophenyl)carbonyl]benzoate (4.8 g, quantitative). MS (EI) for C15H12N2O5: 301 (MH+).

Workup

  1. temperatureto reflux for 18 h
  2. customthe solvent was evaporated
  3. customThe yellow precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8cddf1ac9a5d46b785fc09180ecb1457
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

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