3-Nitrobenzaldehyde → HCID 67442604, compound

HRID 1800875Notes

Reaction equation

HRID 1800875 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH2:11].[N+:13]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=O)([O-:15])=[O:14]>C(O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[N:11]=[CH:19][C:18]1[CH:21]=[CH:22][CH:23]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=1

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 78878Methyl 2-amino-5-chlorobenzoate

Product 1

HCID 67442604HCID 67442604, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-chloro-benzoic acid methyl ester (5.55 g, 30 mmol) and 3-nitro-benzaldehyde (4.99 g, 33 mmol) in ethanol (100 mL) was heated to reflux for 2 h. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 5-chloro-2-[(3-nitro-benzylidene)-amino]-benzoic acid methyl ester (7.2 g, 75%) as a white solid: LC/MS m/e calcd for C15H11ClN2O4 (M+H)+: 319.72, observed: 319.0.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with ether

Sources & evidence

ORD record
ord-d7642bc70acf420a9761e1d956c2e931
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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