HCID 59003019, compound → Ethyl 5-amino-1-methyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate

HRID 561139Notes

Reaction equation

HRID 561139 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[C:7]([N+:16]([O-])=O)[C:8]([F:15])=[C:9]([F:14])[C:10]=2[O:12][CH3:13])[C:5](=[O:19])[C:4]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:3]1>CC(O)=O.[Fe]>[NH2:16][C:7]1[C:8]([F:15])=[C:9]([F:14])[C:10]([O:12][CH3:13])=[C:11]2[C:6]=1[C:5](=[O:19])[C:4]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:3][N:2]2[CH3:1]

Participants

4

Reactant 1

HCID 59003019HCID 59003019, compound

Product 1

HCID 59003029Ethyl 5-amino-1-methyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylateYield 32%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of ethyl 1-methyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (735 mg, 2.15 mmol) and iron powder (600 mg, 10.7 mmol) in AcOH (5 mL) was stirred e at 80° C. for 8 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-methyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (215 mg, 32%) as a yellow solid.

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-3d30b2c866374c64a36db5f7b1002dd3
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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