Ethanol → HCID 10442276, compound

HRID 2079658Notes

Reaction equation

HRID 2079658 reaction equation
[CH2:1](O)C.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[C:8]([N+:15]([O-])=O)[CH:7]=1>[Fe].C(O)(=O)C>[CH3:1][CH2:13][C:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH3:4])=[CH:7][C:8]=1[NH2:15])=[O:14]

Participants

5

Reactant 2

HCID 702EthanolHCID 126437971-(4-Methoxy-2-nitrophenyl)ethan-1-one

Product 1

HCID 10442276HCID 10442276, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a 1:1 mixture of ethanol and acetic acid was added 1-(4-methoxy-2-nitrophenyl)ethanone (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 1-(4-methoxy-2-aminophenyl)ethanone in 85% yield. ES/MS m/z 196 (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-6ee08297004a4054bb0a19e2647d02b2
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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