Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamide

HRID 1992929Notes

Reaction equation

HRID 1992929 reaction equation
[C:1]([C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9](OC)=[O:10])#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl.[CH3:18][NH:19][O:20][CH3:21].[Li]CCCC>>[C:1]([C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([N:19]([CH3:18])[O:20][CH3:21])=[O:10])#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 11333401Methyl 2-(hex-1-yn-1-yl)benzoateHCID 178418339Butyllithium

Product 1

HCID 107767732-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamideYield 77%

Procedure

Treatment of methyl 2-(1-hexyn-1-yl)benzoate (157) (2.29 g, 10.6 mmol) with a mixture of N,O-dimethylhydroxylamine hydrochloride and nBuLi gave 2.0 g (77%) of the title compound (158) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.92 (t, J=7.2 Hz, 3H), 1.40-1.60 (m, 4H), 2.39 (t, J=7.0 Hz, 2H), 3.32 (br s, 3H), 3.50 (br s, 3H), 7.26-7.35 (m, 3H), 7.37-7.45 (m, 1H). LCMS (APCI): m/z 246 (M+H)+.

Sources & evidence

ORD record
ord-83f311921b774dd98a4dd15c314d7d91
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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