HCID 19853360, compound → HCID 19853335, compound

HRID 1607300Notes

Reaction equation

HRID 1607300 reaction equation
C([O:8][C:9]1[C:10]([F:30])=[C:11]([F:29])[CH:12]=[C:13]2[C:18]=1[N:17]([NH:19][CH2:20][CH:21]=[O:22])[CH:16]=[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:14]2=[O:28])C1C=CC=CC=1>C(Cl)(Cl)Cl.CO.[Pd]>[F:29][C:11]1[CH:12]=[C:13]2[C:18](=[C:9]([OH:8])[C:10]=1[F:30])[N:17]([NH:19][CH2:20][CH:21]=[O:22])[CH:16]=[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:14]2=[O:28]

Participants

5

Reactant 1

HCID 19853360HCID 19853360, compound

Product 1

HCID 19853335HCID 19853335, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Ethyl 8-benzyloxy-6,7-difluoro-1-(formylmethylamino)-4-oxo-1,4-dihydro-3-quinolinecarboxylate (330 mg) was hydrogenated over 5% Pd/C (50 mg) in chloroform (14 ml) for 4 hours. The reaction mixture was diluted with methanol (14 ml) and filtered. The filtered cake was washed with chloroform/methanol (1:1). The combined filtrate was evaporated and the residue was recrystallized from ethanol to give 239 mg of ethyl 6,7-difluoro-1-(formylmethylamino)-8-hydroxy-4-oxo-1,4-dihydro-3-quinolinecarboxylate, mp 221°-225° C. (dec.); MS m/z 326 (M+).

Workup

  1. filtrationfiltered
  2. washThe filtered cake was washed with chloroform/methanol (1:1)
  3. customThe combined filtrate was evaporated
  4. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-6314d52854524c3ebb019c30e76b1ecc
Source dataset
uspto-grants-1989_09
Patent number
US04864023

Reaction notes

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