HCID 178476575, compound → HCID 178470164, compound

HRID 2165543Notes

Reaction equation

HRID 2165543 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5](O)(=O)[CH3:6].[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=2)[N:13]=[CH:12][C:11]=1[NH:21]C(=N)C(Cl)(Cl)Cl>C(O)C>[CH2:5]([O:3][C:1]([C:2]1[NH:9][C:10]2[C:19]3[CH:18]=[CH:17][C:16]([F:20])=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:21]=1)=[O:4])[CH3:6]

Participants

3

Reactant 1

HCID 178476575HCID 178476575, compound

Product 1

HCID 178470164HCID 178470164, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.15 g of 4-amino-7-fluoro-3-(trichloroacetimidoylamino)quinoline diacetate (VIII-1) in 120 ml of ethanol was heated under reflux for two hours. The reaction mixture was concentrated under reduced pressure, and the residue was added to ice-water. After being basified with 2N aqueous ammonia, the mixture was extracted with chloroform. The extract was washed with water and brine, and then dried. The chloroform was removed by evaporation. The residue was chromatographed on a column of silica gel with chloroform-methanol (100:1 v/v), whereby 395 mg (yield: 59%) of the titled compound (I e-1) was obtained as crystals. These were recrystallized from chloroform-ethanol to give colorless crystals melting at 238°~240° C. (d).

Workup

  1. temperatureunder reflux for two hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was added to ice-water
  4. extractionthe mixture was extracted with chloroform
  5. washThe extract was washed with water and brine
  6. customdried
  7. customThe chloroform was removed by evaporation
  8. customThe residue was chromatographed on a column of silica gel with chloroform-methanol (100:1 v/v)

Sources & evidence

ORD record
ord-06b6ffa458c0452ba2238ab895e9a56d
Source dataset
uspto-grants-1990_07
Patent number
US04940714

Reaction notes

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