Hydrazine hydrate (1:1) → HCID 136374690, compound

HRID 907862Notes

Reaction equation

HRID 907862 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:13]1[C:22](=O)[C:21]2[C:20]([C:24]([O:26]C)=O)=[CH:19][CH:18]=[CH:17][C:16]=2[NH:15][CH:14]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:35][NH2:36]>CO>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:13]1[C:22]2=[N:35][NH:36][C:24](=[O:26])[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([C:21]=32)[NH:15][CH:14]1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67260357HCID 67260357, compound

Product 1

HCID 136374690HCID 136374690, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(1-benzyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (3.7 g, 8.46 mmol) in hydrazine monohydrate (25 mL) and methanol (100 mL) was stirred at room temperature for 5 h. The resulting mixture was filtered to give 9-(1-benzyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one as a white solid (950 mg, yield 27%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 4.61-4.64 (d, J=11.2 Hz, 1H), 4.99-5.12 (m, 1H), 6.83-6.89 (m, 4H), 7.14-7.28 (m, 1H), 7.36-7.38 (d, J=7.6 Hz, 1H), 7.54-7.58 (t, J=8.0 Hz, 7H), 12.20 (s, 1H). LC-MS (ESI) m/z: 420 (M+1)+.

Workup

  1. filtrationThe resulting mixture was filtered

Sources & evidence

ORD record
ord-cfeef09829084f18955d1e1619e22ff3
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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