Hydrazine hydrate (1:1) → HCID 136385228, compound

HRID 907848Notes

Reaction equation

HRID 907848 reaction equation
[CH:1]([N:4]1[C:8]([CH:9]2[C:18](=O)[C:17]3[C:16]([C:20]([O:22]CC)=O)=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11][CH:10]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:7][N:6]=[CH:5]1)([CH3:3])[CH3:2].O.[NH2:32][NH2:33]>CO>[CH:1]([N:4]1[C:8]([CH:9]2[C:18]3=[N:32][NH:33][C:20](=[O:22])[C:16]4[CH:15]=[CH:14][CH:13]=[C:12]([C:17]=43)[NH:11][CH:10]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:7][N:6]=[CH:5]1)([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67260330HCID 67260330, compound

Product 1

HCID 136385228HCID 136385228, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl 3-(1-isopropyl-1H-imidazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (770 mg, 1.9 mmol) and hydrazine monohydrate (6 ml, 85%) were added in methanol (10 mL) and stirred at 50° C. overnight. The mixture was filtered, and the white solid was washed with methanol and dried to give 9-(1-isopropyl-1H-imidazol-5-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (90 mg, yield 13%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.82-0.84 (d, J=6.8 Hz, 3H), 1.27-1.29 (d, J=6.4 Hz, 3H), 3.30-3.33 (t, J=6.6 Hz, 1H), 4.67-4.70 (d, J=11.2 Hz, 1H), 4.92-4.95 (d, J=11.2 Hz, 1H), 6.80 (s, 1H), 7.01 (s, 1H), 7.16-7.18 (s, 1H), 7.24-7.28 (m, 3H), 7.31 (s, 1H), 7.36-7.39 (m, 3H), 7.55-7.59 (m, 1H); LC-MS (ESI) m/z: 372 (M+1)+.

Workup

  1. filtrationThe mixture was filtered
  2. washthe white solid was washed with methanol
  3. customdried

Sources & evidence

ORD record
ord-4f6069d3785a4e9dbd4d1b0521b6eb55
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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