Hydrazine hydrate (1:1) → HCID 136186316, compound

HRID 1968140Notes

Reaction equation

[CH2:1]([N:3]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH:22]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)[C:21](=O)[C:20]3[C:19]([C:31](OCC)=[O:32])=[CH:18][CH:17]=[CH:16][C:15]=3[NH:14]2)=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2].O.[NH2:37][NH2:38]>CO>[CH2:4]([N:3]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[NH:14][C:15]3[C:20]4[C:21](=[N:37][NH:38][C:31](=[O:32])[C:19]=4[CH:18]=[CH:17][CH:16]=3)[CH:22]2[C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=2)=[CH:9][CH:8]=1)[CH2:1][CH3:2])[CH3:5]

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of ethyl 2-(4-((diethylamino)methyl)phenyl)-4-oxo-3-p-tolyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (320 mg) in hydrazine monohydrate (2 mL, 85%) and methanol (10 mL) was stirred at 30° C. for overnight. Methanol was removed under reduced pressure. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give the title compound (85 mg, yield 29%). LC-MS (ESI) m/z: 439 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.93 (t, 6H), 2.20 (s, 3H), 2.39 (q, 4H), 3.42 (d, 2H), 4.27 (d, J=8.0 Hz, 1H), 4.73 (d, J=8.0 Hz, 1H), 6.98-7.00 (m, 4H), 7.15-7.17 (m, 3H), 7.22-7.24 (m, 2H), 7.35-7.38 (m, 2H), 7.54-7.56 (m, 1H), 12.12 (s, 1H).

Workup

customMethanol was removed under reduced pressure
customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record: ord-6f34570fcd4942ca9a8762f41f9c92ab
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420650B2

Reaction notes

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