Methanamine, N-methoxy-, hydrochloride (1:1) → N-Methyl-N,4-bis(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzamide

HRID 1992888Notes

Reaction equation

HRID 1992888 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=O)=[C:5]([C:13]#[C:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:4]=1.Cl.[CH3:20][NH:21][O:22][CH3:23].[Li]CCCC>>[CH3:20][N:21]([O:22][CH3:23])[C:7](=[O:9])[C:6]1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:13]#[C:14][CH2:15][CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 68534814Methyl 4-(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzoateHCID 178418339Butyllithium

Product 1

HCID 86087188N-Methyl-N,4-bis(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzamideYield 85%

Procedure

Treatment of methyl 4-(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzoate (102) (0.76 g, 3.09 mmol) with a mixture of N,O-dimethylhydroxylamine hydrochloride and nBuLi gave 0.72 g (85%) of the title compound (103) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.02 (d, J=6.6 Hz, 6H), 1.80-1.95 (m, 1H), 2.28 (d, J=6.6 Hz, 2H), 3.28 (br s, 3H), 3.59 (br s, 3H), 3.80 (s, 3H), 6.84 (dd, J1=8.6 Hz, J2=2.5 Hz, 1H), 6.94 (d, J=2.6 Hz, 1H), 7.24 (d, J=8.6 Hz, 1H). LCMS (ESI): m/z 276 (M+H)+.

Sources & evidence

ORD record
ord-14add0c85932412ea9d51d57a948ea50
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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