Hydrochloric Acid → Ethyl 4-amino-2-methoxy-5-nitrobenzoate

HRID 1465805Notes

Reaction equation

HRID 1465805 reaction equation
C([NH:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:18][CH3:19])[CH:6]=1)(=O)C.Cl.[CH2:21](O)C>>[NH2:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:8]([C:9]([O:11][CH2:12][CH3:21])=[O:10])=[C:7]([O:18][CH3:19])[CH:6]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 77723Methyl 4-acetamido-2-methoxy-5-nitrobenzoate

Product 1

HCID 67231122Ethyl 4-amino-2-methoxy-5-nitrobenzoateYield 91%

Procedure

To a solution of methyl 4-acetamido-2-methoxy-5-nitrobenzoate (135 mg, 0.50 mmol) in ethanol 10 ml) was added concentrated hydrochloric acid (0.5 ml) dropwise and the mixture refluxed under nitrogen overnight. The reaction mixture was then cooled, the solvents removed and the residue purified by column chromatography (silica gel), eluting with 1:1 ethyl acetate/hexane to give ethyl 4-amino-2-methoxy-5-nitrobenzoate as a yellow solid (110 mg, 91%).

Workup

  1. temperaturethe mixture refluxed under nitrogen overnight
  2. temperatureThe reaction mixture was then cooled
  3. customthe solvents removed
  4. customthe residue purified by column chromatography (silica gel)
  5. washeluting with 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-bff5e354b34a43b286885d9ce0ff467a
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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