Ethanol → 2-Amino-3-methoxybenzaldehyde

HRID 2079662Notes

Reaction equation

HRID 2079662 reaction equation
C(O)C.[CH3:4][O:5][C:6]1[C:7]([N+:14]([O-])=O)=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10]>[Fe].C(O)(=O)C>[NH2:14][C:7]1[C:6]([O:5][CH3:4])=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]

Participants

5

Reactant 2

HCID 702EthanolHCID 988673-Methoxy-2-nitrobenzaldehyde

Product 1

HCID 139701212-Amino-3-methoxybenzaldehydeYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a 1:1 mixture of ethanol and acetic acid was added 3-methoxy-2-nitrobenzaldehyde (1 eq) and Fe dust (3 eq) was added in portions. The reduction was complete in 3 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 2-amino-3-methoxybenzaldehyde in 85% yield. ES/MS m/z 151 (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-94ecd7cd2b7b4743841f59779ea05d24
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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