Ethanol → HCID 13607495, compound

HRID 1905927Notes

Reaction equation

HRID 1905927 reaction equation
Cl.[NH2:2][CH:3]1[CH:7]([CH3:8])[CH2:6][N:5]([C:9]2[N:18]=[C:17]3[C:12]([C:13](=[O:25])[C:14]([C:22]([OH:24])=[O:23])=[CH:15][N:16]3[CH:19]3[CH2:21][CH2:20]3)=[CH:11][C:10]=2[F:26])[CH2:4]1.S(=O)(=O)(O)O.[CH2:32](O)[CH3:33]>>[NH2:2][CH:3]1[CH:7]([CH3:8])[CH2:6][N:5]([C:9]2[N:18]=[C:17]3[C:12]([C:13](=[O:25])[C:14]([C:22]([O:24][CH2:32][CH3:33])=[O:23])=[CH:15][N:16]3[CH:19]3[CH2:21][CH2:20]3)=[CH:11][C:10]=2[F:26])[CH2:4]1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13607483HCID 13607483, compound

Product 1

HCID 13607495HCID 13607495, compound

Procedure

7-(3-Amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride (6.6 g) was suspended in absolute ethanol. Sulfuric acid (7 g) was added to the suspension and the mixture was refluxed for 1 hour with stirring. After evaporation of ethanol (ca. 20 ml), absolute ethanol (20 ml) was added and the mixture was again refluxed. This operation was repeated three times and then the mixture was refluxed for 15 hours with stirring. After evaporation of ethanol, chloroform and 20% aqueous sodium hydroxide solution was added to the residue, and the mixture was adjusted to pH>9. The organic layer was separated, chloroform was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate to give ethyl 7-(3-amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8naphthyridine-3-carboxylate (4.3 g), m.p. 148°-150.5° C.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customAfter evaporation of ethanol (ca. 20 ml), absolute ethanol (20 ml)
  3. additionwas added
  4. temperaturethe mixture was again refluxed
  5. temperaturethe mixture was refluxed for 15 hours
  6. stirringwith stirring
  7. customAfter evaporation of ethanol, chloroform and 20% aqueous sodium hydroxide solution
  8. additionwas added to the residue
  9. customThe organic layer was separated
  10. customchloroform was evaporated under reduced pressure
  11. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3575e5158de845aca3cca9b7ac371546
Source dataset
uspto-grants-1987_03
Patent number
US04649144

Reaction notes

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