Hydrazine hydrate (1:1) → 8-(4-Fluorophenyl)-9-(thiazol-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3 (7H)-one

HRID 907933Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:17]([C:18]3[S:19][CH:20]=[CH:21][N:22]=3)[C:16](=O)[C:15]3[C:14]([C:24]([O:26]CC)=O)=[CH:13][CH:12]=[CH:11][C:10]=3[NH:9]2)=[CH:4][CH:3]=1.O.[NH2:30][NH2:31]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:9][C:10]3[C:15]4[C:16](=[N:30][NH:31][C:24](=[O:26])[C:14]=4[CH:13]=[CH:12][CH:11]=3)[CH:17]2[C:18]2[S:19][CH:20]=[CH:21][N:22]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of ethyl 2-(4-fluorophenyl)-4-oxo-3-(thiazol-2-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (180 mg) in 85% hydrazine monohydrate (10 mL) and methanol (10 mL) was stirred at 45° C. for overnight. Methanol was removed under reduced pressure. The mixture was filtered and washed with water to give the title compound (3 mg, yield: 2%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 4.88 (d, J=8.0 Hz, 1H), 5.09 (d, J=8.0 Hz, 1H), 7.01 (t, 2H), 7.21 (d, 1H), 7.36-7.40 (m, 2H), 7.47 (d, 1H), 7.59 (d, 1H), 7.65 (t, 1H), 7.74 (d, 1H); 19F-NMR (400 MHz, CD3OD) δ (ppm): −116.36 (s); LC-MS (ESI) m/z: 365 (M+1)+.

Workup

customMethanol was removed under reduced pressure
filtrationThe mixture was filtered
washwashed with water

Sources & evidence

ORD record: ord-81632545e1dd4ca2a2af8a884101eb0d
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012976B2

Reaction notes

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