Phosphorus oxychloride → Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-(2-chloroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 4561

Reaction equation

HRID 4561 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([CH2:17][CH2:18]O)[CH:7]=[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]2=[O:25].P(Cl)(Cl)([Cl:28])=O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([CH2:17][CH2:18][Cl:28])[CH:7]=[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]2=[O:25]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13670063Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 13670067Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-(2-chloroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.5 g (0.01 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate are suspended in 30 ml chloroform, 3 ml of Cl3PO are added, the mixture is kept at room temperature for 2 hours and evaporated to dryness, the residue is redissolved in chloroform, the resulting solution is washed with a sodium bicarbonate solution and then with water and evaporated, and the precipitate is recrystallized from dimethylformamide to give 3.3 g of a solid melting at 254°-256° C.

Workup

  1. customevaporated to dryness
  2. dissolutionthe residue is redissolved in chloroform
  3. washthe resulting solution is washed with a sodium bicarbonate solution
  4. customwith water and evaporated
  5. customthe precipitate is recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-6b9597b166164c3394f566c446f2efe8
Source dataset
uspto-grants-1988_02
Patent number
US04727080

Linked notes

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