Methyl iodide → 2-Amino-4-methoxy-3-methylbenzonitrile

HRID 1443450Notes

Reaction equation

HRID 1443450 reaction equation
[NH2:1][C:2]1[C:9]([CH3:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:12]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[NH2:1][C:2]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 134647162-Amino-4-hydroxy-3-methylbenzonitrile

Product 1

HCID 552964222-Amino-4-methoxy-3-methylbenzonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 76 (12 g, 0.08 mol), K2CO3 (11 g, 0.08 mol) in dry DMF (200 mL) was stirred for 15 min at RT. To this was added MeI (13.6 g, 0.096 mol) and the mixture was stirred for 4 h at RT. The reaction mixture was diluted with water (800 mL), extracted with 30% ethyl acetate in pet. ether (3×300 mL). The combined organic layers were washed with water and brine, dried and concentrated to give a crude product. The crude product was washed with pet. ether to give pure title compound (12 g, 93%).

Workup

  1. stirringthe mixture was stirred for 4 h at RT
  2. extractionextracted with 30% ethyl acetate in pet. ether (3×300 mL)
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a crude product
  7. washThe crude product was washed with pet. ether

Sources & evidence

ORD record
ord-af6077eecb6844ccad987aed4dea18de
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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