N-Methylaniline → N-Methylacetanilide

Reaction equation

[CH:1]([O:4]P(O)OC(C)C)(C)[CH3:2].[CH3:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:11][N:12]([C:1](=[O:4])[CH3:2])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Reactant 2

HCID 7515N-Methylaniline

HCID 558181Dipropan-2-yl hydrogen phosphite

Product 1

HCID 11364N-MethylacetanilideYield 53%

Procedure

Example 34 was repeated, except that 0.05 mole of phosphorous diisopropyl ester was used in place of phosphorous monoethyl ester and 0.05 mole of N-methylaniline was used in place of aniline, to obtain N-methylacetanilide, yield 53% based on N-methylaniline.

Sources & evidence

ORD record: ord-000eec09122c4356b22814905c4f1863
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04173563

Reaction notes

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