2-Methoxy-4-nitrobenzene-1-thiol → 4-Amino-2-methoxybenzene-1-thiol

HRID 856696Notes

Reaction equation

HRID 856696 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[SH:12]>C(O)(=O)C>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([SH:12])=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

3

Reactant 1

HCID 221487412-Methoxy-4-nitrobenzene-1-thiol

Product 1

HCID 193920294-Amino-2-methoxybenzene-1-thiolYield 52.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 2-methoxy-4-nitrobenzenethiol (7.0 g) was added acetic acid (70 ml), reduced iron (21 g) was added to the mixture, and the mixture was stirred for 6 hours at room temperature. The mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-amino-2-methoxybenzenethiol (3.1 g).

Workup

  1. additionwas added to the mixture
  2. filtrationThe mixture was filtered with Celite
  3. washwashed with ethyl acetate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4082bcaf6bfe4ffeb801f5d3bf3cd149
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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