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

HRID 1967968Notes

Reaction equation

HRID 1967968 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]1[CH:14]1[C:23](=O)[C:22]2[C:21]([C:25]([O:27]C)=O)=[CH:20][CH:19]=[CH:18][C:17]=2[NH:16][CH:15]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:36][NH2:37]>>[CH2:1]([N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]1[CH:14]1[C:23]2=[N:36][NH:37][C:25](=[O:27])[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([C:22]=32)[NH:16][CH:15]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67260654methyl 3-(1-benzyl-4-methyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

Product 1

HCID 1363747039-(1-benzyl-4-methyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-oneYield 16%

Procedure

A mixture of methyl 3-(1-benzyl-4-methyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (250 mg, 0.57 mmol) and hydrazine monohydrate (3 mL) was stirred room temperature for 5 h. The resulting mixture was evaporated under reduced pressure to 15 ml and then filtered; the filtrate was concentrated to give 9-(1-benzyl-4-methyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one as a white solid (40 mg, yield 16%). LC-MS (ESI) m/z: 434 (M+1)+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure to 15 ml
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f08cd1ba5f71428894d3d4b8f50f735f
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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