p-Toluenesulfonic acid monohydrate → HCID 9927793, compound

HRID 2209519Notes

Reaction equation

HRID 2209519 reaction equation
C([CH:4]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:12]2[C:11](=[O:23])[CH2:10][CH2:9][CH2:8][C:7]=2[NH:6][C:5]1([C:25]([F:28])([F:27])[F:26])O)(O)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:28][C:25]([F:26])([F:27])[C:5]1[NH:6][C:7]2[CH2:8][CH2:9][CH2:10][C:11](=[O:23])[C:12]=2[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 199589043-carboxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

Product 1

HCID 9927793HCID 9927793, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3-carboxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone (3.17 g) in toluene (150 mL) was treated with p-toluenesulfonic acid monohydrate (0.32 g), the mixture refluxed vigorously under Dean-Stark conditions for 4 hours and then partitioned between water and ethyl acetate. The organic phase was washed (water and brine) and evaporated. The residue was purified by chromatography (hexane/ethyl acetate, 1:1 and methylene chloride/acetonitrile 95:5) to yield the title compound (0.83 g) as a pale yellow solid; mp 215°-216° C.; NMR: 1.77-2.00 (m,2, CH2), 2.16-2.36 (m,2, CH2), 2.50-2.71 (m,2, CH2), 4.79 (d,1, J=4.1, CH), 5.67 (d,1, J=5.4, CH), 7.57-7.67 (m,2, Ar), 8.04 (m,2, Ar), 9.48 (s,1, NH); MS: m/z=338(M). Analysis for C16H13F3N2O3 : Calculated C, 56.81; H, 3.87; N, 8.28; Found: C, 56.74; H, 4.02; N, 8.28.

Workup

  1. temperaturethe mixture refluxed vigorously under Dean-Stark conditions for 4 hours
  2. custompartitioned between water and ethyl acetate
  3. washThe organic phase was washed (water and brine)
  4. customevaporated
  5. customThe residue was purified by chromatography (hexane/ethyl acetate, 1:1 and methylene chloride/acetonitrile 95:5)

Sources & evidence

ORD record
ord-932c0e8e4a0942a29b18cd9b45f2c584
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Reaction notes

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