Ethanol → HCID 70382696, compound

HRID 649143Notes

Reaction equation

HRID 649143 reaction equation
Cl.[NH2:2][CH2:3][C@H:4]1[C@@H:8]([Cl:9])[CH2:7][N:6]([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:26])[C:15]([C:23]([OH:25])=[O:24])=[CH:16][N:17]3[CH:20]3[CH2:22][CH2:21]3)=[CH:12][C:11]=2[F:27])[CH2:5]1.S(=O)(=O)(O)O.[CH2:33](O)[CH3:34]>>[NH2:2][CH2:3][C@H:4]1[C@@H:8]([Cl:9])[CH2:7][N:6]([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:26])[C:15]([C:23]([O:25][CH2:33][CH3:34])=[O:24])=[CH:16][N:17]3[CH:20]3[CH2:22][CH2:21]3)=[CH:12][C:11]=2[F:27])[CH2:5]1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 70383178HCID 70383178, compound

Product 1

HCID 70382696HCID 70382696, compound

Procedure

7-(cis-3-Aminomethyl-4-chloro-1-pyrrolidinyl)1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride was suspended in absolute ethanol. Sulfuric acid was added to the suspension and the mixture was refluxed for 15 hours with stirring. After evaporation of ethanol, chloroform and a 20% aqueous sodium hydroxide solution were added to the residue, and the mixture was adjusted to pH 9. The organic layer was separated and chloroform was evaporated under reduced pressure. The resulting crystals were collected by filtration to give ethyl 7-(cis-3-aminomethyl-4-chloro-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, m.p. 163°-167° C.

Workup

  1. temperaturethe mixture was refluxed for 15 hours
  2. customAfter evaporation of ethanol, chloroform
  3. additiona 20% aqueous sodium hydroxide solution were added to the residue
  4. customThe organic layer was separated
  5. customchloroform was evaporated under reduced pressure
  6. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-708b49dd02dd4c838b0cc1419e2cabb2
Source dataset
uspto-grants-1988_04
Patent number
US04738968

Reaction notes

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