Hydrochloric Acid → HCID 70495892, compound

HRID 2408033Notes

Reaction equation

HRID 2408033 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:18][C:17]([CH3:20])([CH3:19])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:21](NS(C)(=O)=O)=[O:22])[CH:15]=3)[NH:10]2)[CH:6]=[CH:7][CH:8]=1.[OH-:28].[Na+].O.Cl>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:18][C:17]([CH3:20])([CH3:19])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:21]([OH:22])=[O:28])[CH:15]=3)[NH:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59054345HCID 59054345, compound

Product 1

HCID 70495892HCID 70495892, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-[2-(3-methoxy-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (1.0 g, 2.95 mmol), sodium hydroxide (0.59 g, 14.75 mmol), water (15 mL) in acetonitrile (30 mL) was stirred at 60° C. for 12 h. The mixture was neutralized with a 3 N 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-methoxy-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (0.83 g, 90%) as a white solid which was used for next step without further purification: MS (ESI) M+1=312.2.

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-2a4ee65d7dbe4d74bc43bb31211dd707
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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