HCID 54296403, compound → HCID 23369572, compound

HRID 1900710Notes

Reaction equation

HRID 1900710 reaction equation
[CH2:1]([CH:7]1[CH2:16][C:15]2[NH:14][C:13](=[O:17])[CH2:12][CH2:11][C:10]=2[C:9](=[O:18])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C1C2C(CCCC2)CCC1.[Pd]>[CH2:1]([C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13](=[O:17])[NH:14]2)=[C:9]([OH:18])[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 1

HCID 54296403HCID 54296403, compound

Product 1

HCID 23369572HCID 23369572, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7044DecalinSolvent

Conditions

Temperature
200 °C

Procedure

The obtained 7-n-hexyl-1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione (11.0 g) was suspended in decalin (150 ml). To the suspension, 10% palladium-on-carbon (3.7 g) was added, followed by stirring at 200° C. for 17 hours. After completion of the reaction, the insoluble matter was collected by filtration, washed with ether, then extracted with a solvent mixture of chloroform-methanol (2:1). The extract was dried to solidity under reduced pressure. Recrystallization from methanol yielded 9.56 g of 7-n-hexyl-5-hydroxycarbostyril as colorless needles having a melting point of 252°-255° C. (dec.) (87.9%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe insoluble matter was collected by filtration
  3. washwashed with ether
  4. extractionextracted with a solvent mixture of chloroform-methanol (2:1)
  5. customThe extract was dried to solidity under reduced pressure
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-1b007b7a7aa740e4b2a379b560ff3416
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…