HCID 59002836, compound → HCID 59002990, compound

HRID 561130Notes

Reaction equation

HRID 561130 reaction equation
[F:1][C:2]1[C:3]([N+:21]([O-])=O)=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[NH:8][CH:7]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2=[O:20]>CN(C=O)C.[Pd]>[NH2:21][C:3]1[C:2]([F:1])=[C:11]([F:12])[C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[C:5](=[O:20])[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][NH:8]2

Participants

4

Reactant 1

HCID 59002836HCID 59002836, compound

Product 1

HCID 59002990HCID 59002990, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (1.50 g, 4.57 mmol) and 10% Pd/C (40.5 mg) in DMF (20 mL) was stirred under hydrogen atmosphere at room temprature for 14 h. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo. The resulting solid was recrystallized by EtOH, and dried to yield ethyl 5-amino-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (735 mg, 54%) as a pale brown solid.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting solid was recrystallized by EtOH
  4. customdried

Sources & evidence

ORD record
ord-9d35c7ef647544fa84ea8314fd3d2d6d
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

Loading…