P-Anisidine → N-Methyl-m-anisidine

HRID 1856823Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[CH3:10]OC1C=CC(N)=CC=1>>[CH3:10][NH:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[O:2][CH3:1]

Participants

Reactant 2

HCID 7732P-Anisidine

HCID 108243-Methoxyaniline

Product 1

HCID 84349N-Methyl-m-anisidineYield 77%

Procedure

m-Anisidine (Aldrich Chemical Corp.) was substituted for p-anisidine in the procedure described in Journal Chemical Society, London, 1969:2223, Perkin Transactions I., which gave N-methyl-m-anisidine, as an oil, 24.5 g, 77% yield. NMR was consistent with structure. MS: APCI: M+1: 138.2 (M: 137.2).

Sources & evidence

ORD record: ord-d477361a7a0141a18f3c0c674a1d7e4c
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143766

Reaction notes

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