Methanol → Methyl 4-amino-2-nitrobenzoate

HRID 1066866Notes

Reaction equation

HRID 1066866 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].[CH2:14](Cl)Cl.CO>O=S(Cl)Cl>[N+:1]([C:4]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH3:14])=[O:7])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 2357134-Amino-2-nitrobenzoic Acid

Product 1

HCID 14730691Methyl 4-amino-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent2×

Procedure

2-Nitro-4-aminobenzoic acid (261 mg, 1.43 mmol) was dissolved in 1 ml of SOCl2. The solution was refluxed for 1 hour. Excess SOCl2 was removed under reduced pressure and 5 ml of CH2Cl2, 1 ml of MeOH and TEA (0.24 ml, 1.7 mmol) were added to the residue. The reaction mixture was stirred at room temperature for 2 hours. Excess MeOH and TEA were removed and the residue was purified by column chromatography with ethyl acetate/hexane (1/3) to yield the title compound as a yellow solid (316 mg). 1H NMR δ7.69 (d, J=8.5 Hz, 1H), 6.85 (d, J=2.2 Hz, 1H), 6.67 (dd, J=8.3; 2.1 Hz, 1H), 4.31 (b, 2H), 3.94 (s, 3H).

Workup

  1. temperatureThe solution was refluxed for 1 hour
  2. additionwere added to the residue
  3. customExcess MeOH and TEA were removed
  4. customthe residue was purified by column chromatography with ethyl acetate/hexane (1/3)

Sources & evidence

ORD record
ord-4333ba0898504971ab98ad45198844df
Source dataset
uspto-grants-2001_06
Patent number
US06245786B1

Reaction notes

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