Ethyl 5-benzylamino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate → Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 561093Notes

Reaction equation

HRID 561093 reaction equation
C([NH:8][C:9]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]2[C:10]=1[C:11](=[O:30])[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:13][N:14]2[CH:22]1[CH2:24][CH2:23]1)C1C=CC=CC=1>CC(O)=O.[Pd]>[NH2:8][C:9]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]2[C:10]=1[C:11](=[O:30])[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:13][N:14]2[CH:22]1[CH2:23][CH2:24]1

Participants

4

Reactant 1

HCID 14127984Ethyl 5-benzylamino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 14127986Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 5 (5.12 g, 12.3 mmol) in AcOH (200 mL) was hydrogenated under atmospheric pressure over 10% Pd/C (3.0 g) at 50° C. for 2 h. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo to dryness to yield 6 (3.58 g, 89%) which was used crude in the next step.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. concentrationthe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-261af969a35042eeac9aa0739d982470
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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