1,3-Dichloro-2-propanol → Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 1651381Notes

Reaction equation

HRID 1651381 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8][N:9]2[CH:13]2[CH2:15][CH2:14]2)=[CH:4][C:3]=1[F:22].Cl[CH2:24][CH:25]([OH:28])[CH2:26]Cl>N1C=CC=CC=1>[CH:13]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:22])=[C:2]([N:1]4[CH2:26][CH:25]([OH:28])[CH2:24]4)[C:11]=3[F:12])[C:6](=[O:21])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8]2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 72891,3-Dichloro-2-propanolHCID 10709913Ethyl 7-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 15615453Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.8 g (2.60 mmoles) of ethyl 7-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 0.33 g (2.60 mmoles) of 1,3-dichloro-2-propanol and 25 ml of pyridine is agitated for 3 days, protected from light at ambient temperature; then left refluxing for 3 days and more. The solution is concentrated almost to dryness, poured onto water giving a precipitate which is filtered and washed with water. The solid is dried under vacuum, yielding 0.52 g (55%) of ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate. Its melting point and spectroscopic data are identical to those of the derivative obtained according to method A.

Workup

  1. customprotected from light at ambient temperature
  2. waitthen left
  3. temperaturerefluxing for 3 days
  4. concentrationThe solution is concentrated almost to dryness
  5. additionpoured onto water giving a precipitate which
  6. filtrationis filtered
  7. washwashed with water
  8. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-dbf064aea1c14ceea09cd06236bde428
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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