Hydrochloric Acid → HCID 70497486, compound

HRID 2408036Notes

Reaction equation

HRID 2408036 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:17]=1)[CH2:10][C:9]2([CH3:27])[CH3:26])=[O:5])C.[OH-].[Na+].O.Cl>C(#N)C>[CH3:25][S:22]([C:18]1[CH:17]=[C:16]([CH:11]2[CH2:10][C:9]([CH3:27])([CH3:26])[C:8]3[C:13](=[CH:14][CH:15]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=3)[NH:12]2)[CH:21]=[CH:20][CH:19]=1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 70496554HCID 70496554, compound

Product 1

HCID 70497486HCID 70497486, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(3-methanesulfonyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (3.3 g, 8.53 mmol), sodium hydroxide (3.41 g, 85.3 mmol), water (10 mL) in acetonitrile (30 mL) was stirred at 60° C. for 12 h. The mixture was neutralized with a 3 mol/L aqueous hydrochloric acid solution and extracted with ethyl acetate (2×50 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(3-methanesulfonyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (2.76 g, 90%) as a white solid which was used for next step without further purification: MS (ESI) M+1=360.3.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1b5e1558cac45d0965fb8318ce889d1
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

Loading…