Hydrazine hydrate (1:1) → HCID 136385232, compound

HRID 907869Notes

Reaction equation

HRID 907869 reaction equation
O=[C:2]1[C:11]2[C:10]([C:12](OCC)=O)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5][CH:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:3]1[C:23]1[N:24]([CH2:28][CH2:29][CH3:30])[CH:25]=[CH:26][N:27]=1.[OH2:31].[NH2:32][NH2:33]>CO>[C:17]1([CH:4]2[NH:5][C:6]3[C:11]4[C:2](=[N:32][NH:33][C:12](=[O:31])[C:10]=4[CH:9]=[CH:8][CH:7]=3)[CH:3]2[C:23]2[N:24]([CH2:28][CH2:29][CH3:30])[CH:25]=[CH:26][N:27]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67260881HCID 67260881, compound

Product 1

HCID 136385232HCID 136385232, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl 4-oxo-2-phenyl-3-(1-propyl-1H-imidazol-2-yl)-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 in vacuum to obtain 8-phenyl-9-(1-propyl-1H-imidazol-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (260 mg, yield 37%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.59-0.62 (t, J=7.4 Hz, 1H), 1.23-1.40 (m, 2H), 3.62-3.72 (m, 2H), 4.58-4.61 (d, J=11.2 Hz, 1H), 4.97-4.99 (d, J=11.2 Hz, 1H), 6.79 (s, 1H), 6.89 (s, 1H), 7.16-7.59 (m, 8H), 12.15 (s, 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 in vacuum

Sources & evidence

ORD record
ord-fbeed844a63c48df9154f1368c50113d
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

Loading…