Acetic Acid → HCID 12733936, compound

HRID 544239Notes

Reaction equation

HRID 544239 reaction equation
Cl.[OH:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:21])=[C:12]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:13]=2)[C:8](=[O:22])[C:7]([C:23]([OH:25])=[O:24])=[CH:6]1.[C:26](O)(=[O:28])[CH3:27].C(N(CC)CC)C>CN(C=O)C>[OH:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:21])=[C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:26](=[O:28])[CH3:27])[CH2:17][CH2:16]3)[CH:13]=2)[C:8](=[O:22])[C:7]([C:23]([OH:25])=[O:24])=[CH:6]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 12733906HCID 12733906, compound

Product 1

HCID 12733936HCID 12733936, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-hydroxyethyl)-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride 1.50 g (4 millimole), anhydrous acetic acid 0.7 g (7 millimole), triethylamine 0.5 g (5 millimole) and DMF 5 ml was heated at 90°-100° C. for 3 hours under stirring. After cooling, the reaction mixture was evaporated under vacuum, and acidified with acetic acid. The precipitated crystals were collected by filtration, washed successively with water and ethanol and dried. 1.46 g (97%) of 1-(2-hydroxyethyl)-6-fluoro-7-(4-acetyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was obtained as yellowish powders.

Workup

  1. temperaturewas heated at 90°-100° C. for 3 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under vacuum
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed successively with water and ethanol
  6. customdried

Sources & evidence

ORD record
ord-b9cd3da29d96400592e31ab7e8137c5f
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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