O-Methylhydroxylamine hydrochloride → HCID 86754168, compound

HRID 580996Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2([OH:19])[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[C:5]([CH2:20][CH:21]=[CH2:22])[CH:4]=1)=O.[ClH:23].[O:24]([NH2:26])[CH3:25]>C(O)C>[ClH:23].[CH3:25][O:24][N:26]=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2([OH:19])[CH:16]3[CH2:15][CH2:14][N:13]([CH2:18][CH2:17]3)[CH2:12]2)=[C:5]([CH2:20][CH:21]=[CH2:22])[CH:4]=1

Participants

Conditions

Temperature: 25 °C

Procedure

3-[2-(4-formyl-2-allylphenyl)ethynyl]quinuclidin-3-ol (1.0 g) and methoxylamine hydrochloride were dissolved in ethanol (35 ml) and the mixture stirred at 25° C. for 12 hours. The ethanol was evaporated and the residue crystallised from ethyl acetate to give 3-[2-(4-methoxyiminomethyl-2-allylphenyl)ethynyl]quinuclidin-3-ol hydrochloride as a solid, m.p. 143° C.; microanalysis, found: C, 64.7; H, 7.0; N, 8.0% C20H24N2O2HCl. 0.5H2O requires C, 64.9; H, 7.0; N, 7.6% NMR ([CD3 ]2SO/CD3COOD): 1.5-2.3 (5H, m), 3.2 (4H, t), 3.4 (1H, d), 3.6 (1H, dd), 3.9 (3H, s), 5.1 (2H, m), 6.0 (1H, m), 7.5 (3H, m) and 8.2 (1H, s), m/z 325 (M+H).

Workup

customThe ethanol was evaporated
customthe residue crystallised from ethyl acetate

Sources & evidence

ORD record: ord-f4b2621f8e9a4cb6b9b32bea8026c396
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05919793

Reaction notes

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