Zolpidem → 2-(6-Methyl-2-(4-methylphenyl)imidazo(1,2-a)pyridin-3-yl)acetic acid

HRID 230245

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]=[C:15]3[N:10]([CH:11]=[C:12]([CH3:17])[CH:13]=[CH:14]3)[C:9]=2[CH2:18][C:19](N(C)C)=[O:20])=[CH:6][CH:7]=1.[OH-:24].[Na+]>Cl>[CH3:17][C:12]1[CH:13]=[CH:14][C:15]2[N:10]([C:9]([CH2:18][C:19]([OH:20])=[O:24])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)[N:16]=2)[CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a magnetically stirred solution of zolpidem (8.0 g, 26.0 mmol) at 0° C. under Ar atmosphere was added 6N HCl (80 mL). The reaction mixture was refluxed for 18 h. The mixture was cooled to 0° C., and 20% NaOH was added slowly to a pH of 6.5. The white solids were filtered in vacuo to provide the title compound (6.9 g, 94%) as a white solid. 1H NMR (DMSO-d6) δ 2.30 (s, 3H), 2.35 (s, 3H), 3.94 (s, 2H), 7.10 (d, J=9.1 Hz, 1H), 7.25 (d, J=7.8 Hz, 2H), 7.48 (d, J=9.1 Hz, 1H), 7.72 (d, J=7.8 Hz, 2H), 8.18 (s, 1H). 13C-NMR (100 MHz, DMSO-d6) δ 18.4, 21.4, 30.8, 114.8, 116.6, 121.6, 122.9, 127.9, 128.2, 129.8, 132.4, 137.3, 143.0, 143.5, 171.8.

Workup

temperatureThe reaction mixture was refluxed for 18 h
filtrationThe white solids were filtered in vacuo

Sources & evidence

ORD record: ord-b5f2262498c14ee7859769cf7d1b0e44
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566725B2

Linked notes

Loading…