Hydrochloric Acid → HCID 70496057, compound

HRID 2408003Notes

Reaction equation

HRID 2408003 reaction equation
[CH2:1]([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]([C:22]([O:24]C)=[O:23])[CH:17]=1)[CH2:10][C:9]2([CH3:27])[CH3:26])=[O:5])[CH3:2].Cl>O1CCCC1.[OH-].[Li+].O.C(OCC)(=O)C>[CH2:1]([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]([C:22]([OH:24])=[O:23])[CH:17]=1)[CH2:10][C:9]2([CH3:26])[CH3:27])=[O:5])[CH3:2]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 70495900HCID 70495900, compound

Product 1

HCID 70496057HCID 70496057, compoundYield 50%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-(3-methoxycarbonyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (2.5 g, 6.8 mmol) in tetrahydrofuran (20 mL), 2M lithium hydroxide in water (10 mL) was stirred for 4 h at 25° C. The mixture was neutralized with a 2 N aqueous hydrochloric acid solution, diluted with ethyl acetate (100 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(3-carboxy-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (1.2 g, 50%) as a light white solid which was used for next step without further purification: MS (ESI) M+1=354.2.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7b243581cda4f27889cf4110639d2c7
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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