Hydrochloric Acid → HCID 11386597, compound

HRID 859235Notes

Reaction equation

HRID 859235 reaction equation
C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:13](=[O:35])[NH:14][C:15]3[C:20]([C:21]=2[C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=2[O:29][CH3:30])=[CH:19][C:18]([C:31]([F:34])([F:33])[F:32])=[CH:17][CH:16]=3)=[CH:7][CH:6]=1)C.[OH-].[Na+].Cl>C1COCC1.O>[Cl:28][C:26]1[CH:25]=[CH:24][C:23]([O:29][CH3:30])=[C:22]([C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:31]([F:32])([F:33])[F:34])[CH:19]=3)[NH:14][C:13](=[O:35])[C:12]=2[S:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:36])=[O:3])=[CH:6][CH:7]=2)[CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69666250HCID 69666250, compound

Product 1

HCID 11386597HCID 11386597, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.50 g (0.95 mmol) of 4-[4-(5-Chloro-2-methoxy-phenyl)-2-oxo-6-trifluoromethyl-1,2-dihydro-quinolin-3-ylsulfanyl]-benzoic acid ethyl ester in 5 mL of THF and 5 mL of water was added 5.0 mL (5.0 mmol) of 1N NaOH in water. The mixture was stirred for 4 hr, neutralized with 1 N HCl and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated to dryness to afford 0.48 g (100% yield) of the title compound. 1H NMR 400 MHz (DMSOd6) 3.61 (3H, s), 7.19 (4H, m), 7.37 (1H, d, J=2.7 Hz), 7.54 (1H, dd, J=8.8, 2.7 Hz), 7.58 (1H, d, J=8.6 Hz), 7.76 (2H, d, J=8.6 Hz), 7.92 (1H, dd, J=8.8, 1.7 Hz). MS m/z 506 (M+H). HPLC retention time 2.02 min (0% B to 100% B over 2 min at 5 mL/min.; Solvent A=10% MeOH/90% H2O/0.1% TFA, Solvent B=90% MeOH/10% H2O/0.1% TFA; EXTERRA C18 S5 4.6×50 mm column; UV detector at 220 nM).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-1c622034457d4e90aee0799ec721383c
Source dataset
uspto-grants-2006_12
Patent number
US07151180B2

Reaction notes

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