Ammonia → HCID 59003015, compound

HRID 561112Notes

Reaction equation

HRID 561112 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19](O)=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1.C([N:25](CC)CC)C.ClC(OCC)=O.N>CN(C=O)C.O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([NH2:25])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 105668945-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 59003015HCID 59003015, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (4.97 g, 16.0 mmol) in DMF (200 mL), triethylamine (3.35 mL, 24.0 mmol) and ethyl chloroformate (1.84 mL, 19.2 mmol) were added. After stirring at 0° C. for 2 h., 25% aq. NH3 (5 mL) was added and the mixture was stirred at room temperature for 3 h. The reaction mixture was poured into water (1.5 L) and the resulting precipitate was collected by filtration, washed with water and dried to give 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxamide (4.83 g, 97%) as a pale brown solid.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 3 h
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-50199a42d6154f019d7e71419073d900
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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