Ammonium Hydroxide → 4-Amino-3-methylbenzonitrile

HRID 1087124Notes

Reaction equation

HRID 1087124 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[C:5]#[N:6].O.O.Cl[Sn]Cl.[OH-].[NH4+]>C(O)(=O)C.Cl>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([NH2:10])=[C:2]([CH3:1])[CH:3]=1)#[N:6]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 61436Stannous chloride dihydrateHCID 28014343-Methyl-4-nitrobenzonitrile

Product 1

HCID 70103164-Amino-3-methylbenzonitrileYield 61.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a stirred, 25° C. solution of 3-methyl-4-nitrobenzonitrile (24 g, 0.148 mol) in acetic acid (250 mL) under nitrogen was added dropwise a solution of SnCl2.2H2O (133.57 g., 0.592 mol) in concentrated HCl (250 mL). After stirring for 3 hours, the reaction mixture was added carefully to excess cold ammonium hydroxide. The reaction mixture was extracted several times with ethyl ether. The organic extracts were then combined, dried (Na2SO4) and evaporated under reduced pressure to afford 12 g (61%) of the title compound, 4-cyano-2-methylaniline, as a white solid; m.p. 64°-66° C.

Workup

  1. extractionThe reaction mixture was extracted several times with ethyl ether
  2. dry with materialdried (Na2SO4)
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8acaad97ece44b249ba74d83402664d4
Source dataset
uspto-grants-1991_07
Patent number
US05034410

Reaction notes

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