Hydrazine hydrate (1:1) → 4-(9-(4-Fluorophenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)-N,N-dimethylbenzamide

HRID 907938Notes

Reaction equation

HRID 907938 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH:20]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:19](=O)[C:18]3[C:17]([C:29]([O:31]CC)=O)=[CH:16][CH:15]=[CH:14][C:13]=3[NH:12]2)=[CH:7][CH:6]=1)=[O:4].O.[NH2:36][NH2:37]>>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH:20]2[C:19]3=[N:36][NH:37][C:29](=[O:31])[C:17]4[CH:16]=[CH:15][CH:14]=[C:13]([C:18]=43)[NH:12][CH:11]2[C:8]2[CH:7]=[CH:6][C:5]([C:3]([N:2]([CH3:34])[CH3:1])=[O:4])=[CH:10][CH:9]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67261345Ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

Product 1

HCID 1363747244-(9-(4-Fluorophenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)-N,N-dimethylbenzamideYield 24%

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (490 mg, 1 mmol) and hydrazine monohydrate (15 mL) was stirred at 40° C. for 3 h. Then the mixture was cooled to room temperature and filtered to give the title compound (110 mg, yield 24%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.82 (s, 1H), 2.93 (s, 1H), 4.36-4.38 (d, J=9.2 Hz, 1H), 4.78-4.80 (d, J=9.2 Hz, 1H), 7.01-7.03 (m, 2H), 7.14-7.19 (m, 3H), 7.25-7.28 (m, 2H), 7.32-7.40 (m, 3H), 7.45 (s, 1H), 7.56-7.60 (t, J=8 Hz, 1H), 12.17 (s, 1H); LC-MS (ESI) m/z: 429 (M+1)+.

Workup

  1. temperatureThen the mixture was cooled to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-f53386900bed4e618f00bd2e885dd728
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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