p-Toluenesulfonic acid → HCID 19874153, compound

HRID 465392Notes

Reaction equation

HRID 465392 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:18])=[C:11]([NH:14][CH2:15][CH2:16][OH:17])[CH:12]=3)[C:7](=[O:19])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5]2)[CH2:3][CH2:2]1.[C:25]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:18])=[C:11]([N:14]4[CH2:15][CH2:16][O:17][CH2:25]4)[CH:12]=3)[C:7](=[O:19])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6342AcetonitrileHCID 10024DiethoxymethaneHCID 19874191Ethyl 1-cyclopropyl-6-fluoro-7-(2-hydroxyethylamino)-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 19874153HCID 19874153, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 0.67 g of ethyl 1-cyclopropyl-6-fluoro-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. After the reaction mixture was allowed to cool down, 100 ml of chloroform was added to the reaction mixture. The resultant mixture was successively washed 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 successively washed with 5% aq. sodium carbonate solution and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6e4362da8d5a433b81bc67fd38ea933d
Source dataset
uspto-grants-1992_10
Patent number
US05153203

Reaction notes

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