HCID 19603401, compound → HCID 19603330, compound

HRID 1604574Notes

Reaction equation

HRID 1604574 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])C1C=CC=CC=1>[Pd].C(O)C.O1CCOCC1>[CH2:25]([O:24][C:22]([CH2:21][O:20][C:14]1[C:13]2[C:18](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=2)[N:17]=[C:16]([CH3:19])[CH:15]=1)=[O:23])[CH3:26]

Participants

5

Reactant 1

HCID 19603401HCID 19603401, compound

Product 1

HCID 19603330HCID 19603330, compoundYield 55.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-benzyloxy-4-ethoxycarbonylmethoxy-2-methylquinoline (1.30 g) and palladium on carbon (130 mg) in a mixture of ethanol (8 ml) and dioxane (7 ml) was stirred for 3 hours at ambient temperature under hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated in vacuo to give 4-ethoxycarbonylmethoxy-8-hydroxy-2-methylquinoline (539 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4a5db98fffaf43aab6760c5c1da87430
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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