Hydrochloric Acid → HCID 70496288, compound

HRID 2408113Notes

Reaction equation

HRID 2408113 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([F:28])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:16]=1)[CH2:11][C:10]2([CH3:27])[CH3:26])=[O:4].Cl>CO.O1CCCC1.[OH-].[Na+].O>[F:28][C:7]1[CH:8]=[C:9]2[C:14](=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1)[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[CH:16]=1)[CH2:11][C:10]2([CH3:27])[CH3:26]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 70497868HCID 70497868, compound

Product 1

HCID 70496288HCID 70496288, compoundYield 93.8%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of afford 6-fluoro-4,4-dimethyl-2-(3-pyrrolidin-1-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (0.32 g, 0.81 mmol) in methanol (3 mL) and tetrahydrofuran (10 mL), 30% sodium hydroxide in water (1 mL). The reaction mixture 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 6-fluoro-4,4-dimethyl-2-(3-pyrrolidin-1-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (0.28 g, 90%) as a white solid which was used for next step without further purification: MS (ESI) M+1=369.3.

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-329a1c9df22249b4a855a5a6badebea9
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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