Ethanol → HCID 86743975, compound

HRID 1090401Notes

Reaction equation

HRID 1090401 reaction equation
Cl.[NH2:2][OH:3].[OH-:4].[Na+].O=[C:7]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:25])[CH:17]=[CH:18][N:19]3[CH:22]3[CH2:24][CH2:23]3)=[CH:14][C:13]=2[F:26])[CH2:8]1.[CH2:27]([OH:29])C>O>[N:2](=[C:7]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:25])[C:17]([C:27]([OH:29])=[O:4])=[CH:18][N:19]3[CH:22]3[CH2:24][CH2:23]3)=[CH:14][C:13]=2[F:26])[CH2:8]1)[OH:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 443297Hydroxyamine hydrochlorideHCID 86743976HCID 86743976, compound

Product 1

HCID 86743975HCID 86743975, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.8 g (55 mol) of hydroxylamine hydrochloride in 100 ml of water was neutralized by the addition of 55 ml (55 mmol) of 1.0 N sodium hydroxide. To this was added a suspension of 16.5 g (50 mmol) of 7-(3 oxocyclopentyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline acid in a mixture of 150 ml of ethanol and 50 ml (50 mmol) of 1.0 N sodium hydroxide. The reaction mixture was heated at 60° for 4 hours and then at room temperature overnight. The alcohol was removed in vacuo and the aqueous was acidified to pH 2.0 with 6.0 M hydrochloric acid. The solid was removed by filtration, washed with water, and dried in vacuo to give 16.1 g of the title compound.

Workup

  1. additionTo this was added
  2. temperatureThe reaction mixture was heated at 60° for 4 hours
  3. customat room temperature
  4. customovernight
  5. customThe alcohol was removed in vacuo
  6. customThe solid was removed by filtration
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-316d74a3c11844919876d2d15535292a
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

Loading…