Ethanol → Methyl 3-amino-4-formylbenzoate

HRID 2079650Notes

Reaction equation

HRID 2079650 reaction equation
C(O)C.[CH3:4][O:5][C:6](=[O:18])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[C:9]([N+:15]([O-])=O)[CH:8]=1>[Fe].C(O)(=O)C>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([C:6]([O:5][CH3:4])=[O:18])=[CH:8][C:9]=1[NH2:15])=[O:14]

Participants

5

Reactant 2

HCID 702EthanolHCID 3457222Methyl 4-formyl-3-nitrobenzoate

Product 1

HCID 18412577Methyl 3-amino-4-formylbenzoateYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a 1:1 mixture of ethanol and acetic acid was added methyl4-formyl-3-nitrobenzoate (1 eq) and Fe dust (3 eq) was added in portions. The reduction was complete in 1 h. The reaction mixture was filtered and then concentrated and partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate and dried and concentrated to give methyl 4-formyl-3-aminobenzoate in 85% yield. ES/MS m/z 180 (MH+).

Workup

  1. additionwas added in portions
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated sodium bicarbonate
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-76a3ef8ccaea454cb8b92c8d37c8715c
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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