Ammonium formate → 4-chloro-1-N-methylbenzene-1,2-diamine
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:10]([O-])=O)[CH:3]=1.C([O-])=O.[NH4+]>C(O)C.[Zn]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:6][CH3:7])=[CH:8][CH:9]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 4-chloro-N-methyl-2-nitroaniline (713 mg, 3.8 mmol) in ethanol (10 mL) is added ammonium formate (1.2 g, 19 mmol) followed by zinc dust (745 mg, 11.5 mmol). The reaction is heated to 50° C. for 2 h. The room temperature suspension is filtered through a bed of Celite and the filtrate is rinsed with additional methanol (10 mL). The filtrate is concentrated to afford the title compound (592 mg, 89%) as an oil which was used in the next step without purification
Workup
- filtrationThe room temperature suspension is filtered through a bed of Celite
- washthe filtrate is rinsed with additional methanol (10 mL)
- concentrationThe filtrate is concentrated
Sources & evidence
- ORD record
- ord-2b3b6781a45d457fa1616e7ac6df4580
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150577B2
Reaction notes
Loading…