Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86087094, compound

HRID 1992922Notes

Reaction equation

HRID 1992922 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:7]=2[C:8]([O:10]C)=O)[CH2:3][CH2:2]1.Cl.[CH3:19][NH:20][O:21][CH3:22].[Li]CCCC>>[CH:1]1([C:4]#[C:5][C:6]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:7]=2[C:8]([N:20]([CH3:19])[O:21][CH3:22])=[O:10])[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 68539387HCID 68539387, compoundHCID 178418339Butyllithium

Product 1

HCID 86087094HCID 86087094, compoundYield 86%

Procedure

Treatment of methyl 2-(cyclopropylethynyl)-4-(methyloxy)benzoate (149) (0.49 g, 2.13 mmol) with a mixture of N,O-dimethylhydroxylamine hydrochloride and nBuLi gave 0.47 g (86%) of the title compound (150) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.70-0.90 (m, 4H), 1.40-1.50 (m, 1H), 3.28 (br s, 3H), 3.63 (br s, 3H), 3.80 (s, 3H), 6.83 (dd, J1=8.5 Hz, J2=2.6 Hz, 1H), 6.91 (d, J=2.4 Hz, 1H), 7.24 (d, J=8.6 Hz, 1H). LCMS (ESI): m/z 260 (M+H)+.

Sources & evidence

ORD record
ord-0455a812eb8c48d6b1949fa8b2acf625
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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