8,8-dimethyl-2-(4-nitrophenyl)-5,6,7,8-tetrahydro-1H-imidazo[4,5-g]quinolin-6-one → HCID 19896769, compound

HRID 1196904Notes

Reaction equation

HRID 1196904 reaction equation
[CH3:1][C:2]1([CH3:25])[C:11]2[CH:10]=[C:9]3[NH:12][C:13]([C:15]4[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=4)=[N:14][C:8]3=[CH:7][C:6]=2[NH:5][C:4](=[O:24])[CH2:3]1>CO.[Pd]>[CH3:1][C:2]1([CH3:25])[C:11]2[CH:10]=[C:9]3[NH:12][C:13]([C:15]4[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=4)=[N:14][C:8]3=[CH:7][C:6]=2[NH:5][C:4](=[O:24])[CH2:3]1

Participants

4

Reactant 1

HCID 198968048,8-dimethyl-2-(4-nitrophenyl)-5,6,7,8-tetrahydro-1H-imidazo[4,5-g]quinolin-6-one

Product 1

HCID 19896769HCID 19896769, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

13 g. 8,8-dimethyl-2-(4-nitrophenyl)-5,6,7,8-tetrahydro-1H-imidazo[4,5-g]quinolin-6-one (see Example 30i)) were hydrogenated in methanol in the presence of palladium/charcoal. After filtering off the catalyst, the filtrate was evaporated and the residue recrystallized from 2N hydrochloric acid/ethanol (1:1 v/v) to give 7.8 g. of the title compound in the form of its hydrochloride; m.p. 305°-308° C. (decomp.).

Workup

  1. filtrationAfter filtering off the catalyst
  2. customthe filtrate was evaporated
  3. customthe residue recrystallized from 2N hydrochloric acid/ethanol (1:1 v/v)
  4. customto give 7.8 g

Sources & evidence

ORD record
ord-442556e1ee7e428399932a019052b8a6
Source dataset
uspto-grants-1992_05
Patent number
US05116843

Reaction notes

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