Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86087169, compound

HRID 1992956Notes

Reaction equation

[C:1]([C:11]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:12]=1[C:13]([O:15]C)=O)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Cl.[CH3:24][NH:25][O:26][CH3:27].[Li]CCCC>>[C:1]([C:11]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:12]=1[C:13]([N:25]([CH3:24])[O:26][CH3:27])=[O:15])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

HCID 68536763HCID 68536763, compound

HCID 178418339Butyllithium

Product 1

HCID 86087169HCID 86087169, compoundYield 94%

Procedure

Treatment of methyl 2-(1-decyn-1-yl)-4-(methyloxy)benzoate (191) (0.78 g, 2.58 mmol) with a mixture of N,O-dimethylhydroxylamine hydrochloride and nBuLi gave 0.80 g (94%) of the title compound (192) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.85-0.90 (m, 3H), 1.20-1.37 (m, 8H), 1.37-1.50 (m, 2H), 1.55-1.65 (m, 2H), 2.38 (t, J=7.2 Hz, 2H), 3.28 (br s, 3H), 3.61 (br s, 3H), 3.80 (s, 3H), 6.84 (dd, J1=8.5 Hz, J2=2.5 Hz, 1H), 6.93 (d, J=2.4 Hz, 1H), 7.24 (d, J=8.6 Hz, 1H). LCMS (ESI): m/z 332 (M+H)+.

Sources & evidence

ORD record: ord-044d4f218aaf4272ab0da7482fc02f86
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649093B2

Reaction notes

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