Ethanolamine → HCID 479008, compound

HRID 898112Notes

Reaction equation

HRID 898112 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:22])[C:11]([C:19]([OH:21])=[O:20])=[CH:12][N:13]2[CH:16]2[CH2:18][CH2:17]2)=[CH:8][C:7]=1[F:23].CO>CN1C(=O)CCC1>[CH:16]1([N:13]2[C:14]3[C:9](=[CH:8][C:7]([F:23])=[C:6]([NH:4][CH2:3][CH2:1][OH:2])[CH:15]=3)[C:10](=[O:22])[C:11]([C:19]([OH:21])=[O:20])=[CH:12]2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 887MethanolHCID 483180Fluoroquinolonic acid

Product 1

HCID 479008HCID 479008, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of ethanolamine (55.5 ml) in N-methyl pyrrolidinone (500 ml) at 95° C., 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (50.0 g) was slowly added under vigorous stirring. The temperature was increased to 105° C. and the reaction mixture was stirred at this temperature for 22 hours. The reaction mixture was cooled to about 60° C. and poured into MeOH (800 ml). This mixture was stirred in an ice bath and the precipitate was filtered off and dried affording a mixture of Intermediate 29A and Intermediate 29B (49 g ) in a 1:1 ratio.

Workup

  1. temperatureThe reaction mixture was cooled to about 60° C.
  2. stirringThis mixture was stirred in an ice bath
  3. filtrationthe precipitate was filtered off
  4. customdried
  5. customaffording

Sources & evidence

ORD record
ord-87edd40d92764d4da2d88f77fdfda6e1
Source dataset
uspto-grants-2008_04
Patent number
US07351696B2

Reaction notes

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