p-Toluenesulfonic acid → HCID 19874190, compound

HRID 465393Notes

Reaction equation

HRID 465393 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:19])=[C:11]([NH:15][CH2:16][CH2:17][OH:18])[C:12]=3[F:14])[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1.[C:26]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCOCC)C.C(#N)C>C(Cl)(Cl)Cl>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:19])=[C:11]([N:15]4[CH2:16][CH2:17][O:18][CH2:26]4)[C:12]=3[F:14])[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6342AcetonitrileHCID 10024DiethoxymethaneHCID 19874161HCID 19874161, compound

Product 1

HCID 19874190HCID 19874190, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 0.70 g of ethyl 1-cyclopropyl-6,8-difluoro-7-(2-hydroxyethylamino)-1,4-dihydro-4-oxoquinoline-3-carboxylate, 0.08 g of p-toluenesulfonic acid, 2.08 g of diethoxymethane and 20 ml of acetonitrile was stirred for 3 hours under reflux. The reaction mixture was allowed to cool down, followed by the addition of 100 ml of chloroform. The resultant mixture was washed successively with 5% aq. sodium carbonate solution and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated.

Workup

  1. temperatureunder reflux
  2. temperatureto cool down
  3. washThe resultant mixture was washed successively with 5% aq. sodium carbonate solution and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-088503c2682245e996ef7b519e2a1c32
Source dataset
uspto-grants-1992_10
Patent number
US05153203

Reaction notes

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