HCID 14209949, compound → HCID 14209956, compound

HRID 1196883Notes

Reaction equation

HRID 1196883 reaction equation
[CH3:1][C:2]1([CH3:27])[C:11]2[C:6](=[CH:7][C:8]([N+:23]([O-])=O)=[C:9]([NH:12][C:13](=O)[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:10]=2)[NH:5][C:4](=[O:26])[CH2:3]1>[Pd].C(O)C>[CH3:1][C:2]1([CH3:27])[C:11]2[CH:10]=[C:9]3[NH:12][C:13]([C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)=[N:23][C:8]3=[CH:7][C:6]=2[NH:5][C:4](=[O:26])[CH2:3]1

Participants

4

Reactant 1

HCID 14209949HCID 14209949, compound

Product 1

HCID 14209956HCID 14209956, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6.8 g. (18.4 mmole) 4,4-dimethyl-6-(4-methoxybenzoylamino)-7-nitro-1,2,3,4-tetrahydroquinolin-2-one were hydrogenated in 200 ml. ethanol in the presence of 0.6 g. 10% palladium on charcoal. After filtering off of the catalyst, the filtrate was mixed with 15 ml. concentrated hydrochloric acid and boiled under reflux for 20 hours. The evaporation residue was mixed with water and ammonia, extracted with methylene chloride/methanol (20:1 v/v), purified over silica gel (elution agent:methylene chloride/ammonia-saturated methanol; 20:1 v/v) and recrystallized from ethanol to give 3.5 g. (60% of theory) of the title compound; m.p. 235°-238° C.

Workup

  1. filtrationAfter filtering off of the catalyst
  2. additionthe filtrate was mixed with 15 ml
  3. temperatureunder reflux for 20 hours
  4. additionThe evaporation residue was mixed with water and ammonia
  5. extractionextracted with methylene chloride/methanol (20:1 v/v)
  6. custompurified over silica gel (elution agent:methylene chloride/ammonia-saturated methanol; 20:1 v/v)
  7. customrecrystallized from ethanol
  8. customto give 3.5 g

Sources & evidence

ORD record
ord-eba2beee8c4c4332b644975ac71eb099
Source dataset
uspto-grants-1992_05
Patent number
US05116843

Reaction notes

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