Hydrazine hydrate (1:1) → HCID 136385170, compound

HRID 907855Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][C:3]([CH:6]2[C:15](=O)[C:14]3[C:13]([C:17]([O:19]CC)=O)=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][CH:7]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:2]1.O.[NH2:29][NH2:30]>CO>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]2[C:15]3=[N:29][NH:30][C:17](=[O:19])[C:13]4[CH:12]=[CH:11][CH:10]=[C:9]([C:14]=43)[NH:8][CH:7]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:2]1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of ethyl 3-(furan-3-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (80 mg) in 85% hydrazine monohydrate (10 mL) and methanol (10 mL) was stirred at 45° C. overnight. Methanol was removed under reduced pressure. The crude product was purified by prep-HPLC to give 9-(furan-3-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (5 mg, yield 7%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 4.19 (d, J=8.0 Hz, 1H), 4.67 (d, J=8.0 Hz, 1H), 6.26 (s, 1H), 7.07-7.21 (m, 7H), 7.30 (s, 1H), 7.27 (m, 1H), 7.41 (d, 1H), 7.51 (m, 1H); LC-MS (ESI) m/z: 330 (M+1)+.

Workup

customMethanol was removed under reduced pressure
customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-8fef3ee84e2341b98a2e27b0bb6d12b1
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012976B2

Reaction notes

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