Dimethylformamide → 2-Amino-4-methoxy-3-methylbenzonitrile

HRID 531384Notes

Reaction equation

HRID 531384 reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[C:9]([O-:12])([O-])=O.[K+].[K+].CI.[CH3:17][N:18](C=O)C>O>[NH2:8][C:1]1[C:6]([CH3:7])=[C:5]([O:12][CH3:9])[CH:4]=[CH:3][C:2]=1[C:17]#[N:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12878168Hept-6-en-1-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-b3dda518b68447feb66821f0ad349f3e
Source dataset
uspto-grants-2016_05
Patent number
US09353103B2

Reaction notes

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