Ethyl Acetate → 4-Amino-5-hydroxy-2-methylbenzonitrile

HRID 1968980Notes

Reaction equation

HRID 1968980 reaction equation
[OH:1][C:2]1[C:3]([N+:11]([O-])=O)=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].CCOC(C)=O>CCO>[NH2:11][C:3]1[C:2]([OH:1])=[CH:9][C:6]([C:7]#[N:8])=[C:5]([CH3:10])[CH:4]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 594441745-Hydroxy-2-methyl-4-nitrobenzonitrile

Product 1

HCID 552844024-Amino-5-hydroxy-2-methylbenzonitrileYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-hydroxy-2-methyl-4-nitrobenzonitrile (D91, 185 mg, 1.04 mmol) was dissolved in EtOH:EtOAc (24 mL, 1:1) and was reduced using an H-Cube (full H2 mode, 25° C., 1 mL/min). The reaction was concentrated by rotary evaporation to give 4-amino-5-hydroxy-2-methylbenzonitrile (D92, 152 mg, 95%) as a pale yellow solid.

Workup

  1. customan H-Cube (full H2 mode, 25° C., 1 mL/min)
  2. concentrationThe reaction was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-19abe163285f44ef869912ec64b69e71
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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