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

HRID 2367157Notes

Reaction equation

HRID 2367157 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-7fe4c9b4f3614ee59099db02e75ffa7c
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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