Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86087198, compound
Reaction equation
[C:1]([C:8]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:9]=1[C:10]([O:12]C)=O)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl.[CH3:21][NH:22][O:23][CH3:24].[Li]CCCC>>[C:1]([C:8]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:9]=1[C:10]([N:22]([CH3:21])[O:23][CH3:24])=[O:12])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]Participants
4
Procedure
Treatment of methyl 2-(1-heptyn-1-yl)-4-(methyloxy)benzoate (110) (0.67 g, 2.57 mmol) with a mixture of N,O-dimethylhydroxylamine hydrochloride and nBuLi gave 0.58 g (78%) of the title compound (111) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 0.93 (t, J=7.0 Hz, 3H), 1.30-1.50 (m, 4H), 1.60-1.70 (m, 2H), 2.41 (t, J=7.1 Hz, 2H), 3.31 (br s, 3H), 3.64 (br s, 3H), 3.83 (s, 3H), 6.86 (dd, J1=8.5 Hz, J2=2.5 Hz, 1H), 6.96 (d, J=2.6 Hz, 1H), 7.27 (d, J=8.6 Hz, 1H). LCMS (ESI): m/z 290 (M+H)+.
Sources & evidence
- ORD record
- ord-c75f0b63216841a2b7b088b69119c958
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07649093B2
Reaction notes
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