HCID 59002963, compound → Ethyl 5-amino-1-benzyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate

HRID 561133Notes

Reaction equation

HRID 561133 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([N+:22]([O-])=O)[C:14]([F:21])=[C:15]([F:20])[C:16]=2[O:18][CH3:19])[C:11](=[O:25])[C:10]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.[Fe]>[NH2:22][C:13]1[C:14]([F:21])=[C:15]([F:20])[C:16]([O:18][CH3:19])=[C:17]2[C:12]=1[C:11](=[O:25])[C:10]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:9][N:8]2[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 59002963HCID 59002963, compound

Product 1

HCID 59002850Ethyl 5-amino-1-benzyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylateYield 60.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 1-benzyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (2.0 g, 4.78 mmol) and iron powder (2.67 g, 47.8 mmol) in AcOH (20 mL) was stirred e at 90° C. for 5 h. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo. The residue was diluted with water and basified with aq. NaOH. The mixture was filtrated over celite and washed with CH2Cl2. The resulting solution was extracted with CH2Cl2. The organic layer washed with water, brine, and then dried. The solvent was removed and the resulting solid washed with EtOH, dried to yield ethyl 5-amino-1-benzyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (1.12 g, 60%) as a yellow solid. M.p. 134-135° C.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with water and basified with aq. NaOH
  4. filtrationThe mixture was filtrated over celite
  5. washwashed with CH2Cl2
  6. extractionThe resulting solution was extracted with CH2Cl2
  7. washThe organic layer washed with water, brine
  8. customdried
  9. customThe solvent was removed
  10. washthe resulting solid washed with EtOH
  11. customdried

Sources & evidence

ORD record
ord-5ec035cdc54b4d229e85eb3017cec639
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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