Hydrochloric Acid → Methyl 4-(methylamino)-3-nitrobenzoate

HRID 1410208Notes

Reaction equation

HRID 1410208 reaction equation
Cl.[CH3:2][NH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14].[CH3:16]N(C=O)C>CO>[CH3:2][NH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:16])=[O:9])=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 2834754-(Methylamino)-3-nitrobenzoic acid

Product 1

HCID 7650848Methyl 4-(methylamino)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl was bubbled through a mixture of 4-methylamino-3-nitrobenzoic acid (7.41 g, 37.8 mmol), DMF (60 mL) and MeOH (250 mL) at reflux for 10 h. The mixture was allowed to cool, filtered and concentrated. NaHCO3 (aq, sat) was added to the residue which was extracted with EtOAc. The combined extracts were washed with brine, dried and concentrated to give the sub-title compound.

Workup

  1. temperatureat reflux for 10 h
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionNaHCO3 (aq, sat) was added to the residue which
  6. extractionwas extracted with EtOAc
  7. washThe combined extracts were washed with brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3ee22fb65ab14ac781f0b08e53cfef0e
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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