4-Hydroxypyrrolidine → 1-Cyclopropyl-6,8-difluoro-7-(3-hydroxypyrrolidin-1-yl)-4-oxo-quinoline-3-carboxylic acid

HRID 978204Notes

Reaction equation

HRID 978204 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[OH:21][CH:22]1[CH2:26][CH2:25][NH:24][CH2:23]1>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:24]4[CH2:25][CH2:26][CH:22]([OH:21])[CH2:23]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 4654501-Cyclopropyl-6,8-difluoro-7-(3-hydroxypyrrolidin-1-yl)-4-oxo-quinoline-3-carboxylic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.1 g (7.8 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid, 20 ml acetonitrile, 1.2 g (7.8 mmole) 1,8-diazobicyclo[5.4.0]undec-7-ene and 0.7 g (7.8 mmole) of 3-hydroxypyrrolidine was refluxed for 2.5 hours. The reaction was allowed to cool and stirred at room temperature for 48 hours. The resulting precipitate was filtered, washed with diethyl ether, then taken up in isopropyl alcohol. The solid was filtered and washed with ether until dry to give 2.0 g of the title compound, mp 276°-278° C.

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. temperatureto cool
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with diethyl ether
  5. filtrationThe solid was filtered
  6. washwashed with ether
  7. customuntil dry

Sources & evidence

ORD record
ord-3afccf74138644c68cfdfffc61a84e43
Source dataset
uspto-grants-1987_05
Patent number
US04663457

Reaction notes

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