5-(Methylthio)-2-nitroaniline → 4-(Methylthio)benzene-1,2-diamine
Reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-])=O)=[C:7]([CH:9]=1)[NH2:8]>C(O)(=O)C.[Zn]>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:10])=[C:7]([NH2:8])[CH:9]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
A solution of 5-methylthio-2-nitroaniline (50 mg; 0.27 mmol) in acetic acid (2 ml) was heated to 85° C. Zinc powder (71 mg; 1.09 mmol) was then added portionwise over 15 minutes and the resulting solution was maintained at 85° C. for 2 hours. The hot reaction mixture was then filtered through celite and the filter cake washed with hot acetic acid (10 ml). The filtrate was evaporated to dryness to give crude 4-methylthio-1,2-phenylenediamine (42 mg, 100%). This was used directly in the next step without purification.
Workup
- filtrationThe hot reaction mixture was then filtered through celite
- washthe filter cake washed with hot acetic acid (10 ml)
- customThe filtrate was evaporated to dryness
Sources & evidence
- ORD record
- ord-3d418b27026344a5aef1953b0a290887
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815895B2
Reaction notes
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