Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86087083, compound

HRID 1992916Notes

Reaction equation

HRID 1992916 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=O.Cl.[CH3:17][NH:18][O:19][CH3:20].[Li]CCCC>>[CH3:17][N:18]([O:19][CH3:20])[C:8](=[O:10])[C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[C:5]#[C:4][CH2:3][O:2][CH3:1]

Participants

4

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 14899688HCID 14899688, compoundHCID 178418339Butyllithium

Product 1

HCID 86087083HCID 86087083, compoundYield 48%

Procedure

Treatment of methyl 2-[3-(methyloxy)-1-propyn-1-yl]benzoate (142) (0.64 g, 3.13 mmol) with a mixture of N,O-dimethylhydroxylamine hydrochloride and nBuLi gave 0.35 g (48%) of the title compound (143) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 3.32 (br s, 3H), 3.43 (s, 3H), 3.50 (br s, 3H), 4.30 (s, 2H), 7.25-7.40 (m, 3H), 7.45-7.55 (m, 1H). LCMS (ESI): m/z 234 (M+H)+.

Sources & evidence

ORD record
ord-28a83e18112442729d34691256b2651b
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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