Ammonium Carbonate → Ethyl 6-amino-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate

HRID 561156Notes

Reaction equation

HRID 561156 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:18]([O-:20])=[O:19])[C:10](F)=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[NH4+:31].[NH4+]>CN(C=O)C>[NH2:31][C:10]1[C:9]([N+:18]([O-:20])=[O:19])=[C:8]2[C:13](=[C:12]([O:14][CH3:15])[C:11]=1[F:16])[N:4]([CH:1]1[CH2:3][CH2:2]1)[CH:5]=[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:7]2=[O:21]

Participants

4

Reactant 2

HCID 517111Ammonium CarbonateHCID 10666701Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate

Product 1

HCID 59002951Ethyl 6-amino-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylateYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (5.00 g, 13.5 mmol) and ammonium carbonate (11.7 g, 122 mmol) in DMF (50 mL) was stirred at 90° C. for 18 h. After the reaction mixture was poured into ice-water, the crude product was extracted with CH2Cl2, washed with brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product washed with EtOH and dried to yield ethyl 6-amino-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (2.55 g, 52%) as a yellow solid.

Workup

  1. extractionthe crude product was extracted with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed in vacuo
  5. washThe crude product washed with EtOH
  6. customdried

Sources & evidence

ORD record
ord-85f518514b554e1db6f8d527d3bec36a
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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