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

HRID 907784Notes

Reaction equation

HRID 907784 reaction equation
[CH3:1][O:2][CH:3]([O:31][CH3:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:18](=O)[C:17]3[C:16]([C:27]([O:29]C)=O)=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11]2)=[CH:6][CH:5]=1.O.[NH2:34][NH2:35]>>[CH3:1][O:2][CH:3]([O:31][CH3:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[NH:11][C:12]3[C:17]4[C:18](=[N:34][NH:35][C:27](=[O:29])[C:16]=4[CH:15]=[CH:14][CH:13]=3)[CH:19]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67260583Methyl 2-(4-(dimethoxymethyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

Product 1

HCID 1363746658-(4-(Dimethoxymethyl)phenyl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-oneYield 78%

Conditions

Temperature
40 °C

Procedure

To methyl 2-(4-(dimethoxymethyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (120 mg, 0.28 mmol) was added hydrazine monohydrate (20 mL) and the mixture was stirred under 40° C. for 3 h. The resulting mixture was evaporated under reduced pressure to 10 ml and then filtered, 89 mg of solid of 8-(4-(dimethoxymethyl)phenyl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one was obtained (yield: 78%). LC-MS (ESI) m/z: 414 (M+1)+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure to 10 ml
  2. filtrationfiltered

Sources & evidence

ORD record
ord-f4dc75c3b29f4783991ba4447954e649
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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