HCID 14209949, compound → HCID 14209956, compound

HRID 1031437Notes

Reaction equation

HRID 1031437 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-methoxy- benzoylamino)-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 recrystallised 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. customrecrystallised from ethanol
  8. customto give 3.5 g

Sources & evidence

ORD record
ord-2aab5e94658d477196530232193d9be0
Source dataset
uspto-grants-1990_09
Patent number
US04954498

Reaction notes

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