Ammonium Hydroxide → 3,5-Diamino-4-methylbenzonitrile
Reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([CH3:12])=[C:5]([N+:13]([O-])=O)[CH:4]=1)#[N:2].[Sn].[OH-].[NH4+]>Cl.C(O)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH2:13])[C:6]([CH3:12])=[C:7]([NH2:9])[CH:8]=1)#[N:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A solution of 4-cyano-2,6-dinitrotoluene (8.55 g) in concentrated hydrochloric acid (70 mL) and glacial acetic acid (10 mL) is treated with tin metal (granules, 14.66 g), which is added slowly so that the temperature does not exceed 50° C. The reaction is stirred at 50° C. for 2.5 hours, then poured into ice and basified to pH=11 with concentrated ammonium hydroxide. The products are extracted with ethyl acetate (5×300 mL). The combined extracts are dried over sodium sulfate and rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 50% ethyl acetate/hexane to afford 4-cyano-2,6-diaminotoluene as a yellow solid.
Workup
- additionis added slowly so that the temperature
- customdoes not exceed 50° C
- extractionThe products are extracted with ethyl acetate (5×300 mL)
- dry with materialThe combined extracts are dried over sodium sulfate and rotary evaporated
- customThe residue is purified by flash chromatography on silica gel
- washeluting with 50% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-6953c60b594a4eb9a7ee139aa7b12d0c
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05716966
Reaction notes
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