p-Toluenesulfonic acid → HCID 19874156, compound

HRID 465395Notes

Reaction equation

HRID 465395 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:20])[C:10]([F:19])=[C:11]([NH:15][CH2:16][CH2:17][OH:18])[C:12]=3[F:14])[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.[C:27]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](=[C:9]([F:20])[C:10]([F:19])=[C:11]([N:15]4[CH2:16][CH2:17][O:18][CH2:27]4)[C:12]=3[F:14])[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6342AcetonitrileHCID 10024DiethoxymethaneHCID 19874168HCID 19874168, compound

Product 1

HCID 19874156HCID 19874156, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 0.74 g of ethyl 1-cyclopropyl-5,6,8-trifluoro-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-dab88556ffe84e2b942eb98310aa6fb6
Source dataset
uspto-grants-1992_10
Patent number
US05153203

Reaction notes

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