Methyl iodide → N-Methyl-4-anisidine

HRID 1053566Notes

Reaction equation

HRID 1053566 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.I[CH3:11]>C(#N)C.C(N(C(C)C)CC)(C)C>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][CH3:11])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 7732P-Anisidine

Product 1

HCID 22250N-Methyl-4-anisidine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-methoxy-aniline (0.65 g, 5.28 mmol) and iodomethane (0.33 mL, 5.28 mmol) in Acetonitrile (10.0 mL), diisopropylethylamine was added (1.50 mL, 10.56 mmol) dropwise. After the addition was complete, the reaction was stirred at 60° C. for 12 hours. The reaction mixture was concentrated and the crude product 6a was used directly for the next step.

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-437361b346c44e15941fc32df36de88e
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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