Hydrochloric Acid → HCID 70496357, compound

HRID 2408078Notes

Reaction equation

HRID 2408078 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:17]=[N:18][CH:19]=[C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[CH:21]=1)[CH2:10][C:9]2([CH3:29])[CH3:28])=[O:5])C.Cl>CO.O1CCCC1.[OH-].[Na+].O>[CH3:28][C:9]1([CH3:29])[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=2)[NH:12][CH:11]([C:16]2[CH:17]=[N:18][CH:19]=[C:20]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)[CH:21]=2)[CH2:10]1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 70497403HCID 70497403, compound

Product 1

HCID 70496357HCID 70496357, compoundYield 81.6%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4,4-dimethyl-2-(5-morpholin-4-yl-pyridin-3-yl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (0.40 g, 1.0 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 4,4-dimethyl-2-(5-morpholin-4-yl-pyridin-3-yl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (0.30 g, 81%) as a white solid which was used for next step without further purification: MS (ESI) M+1=368.2;

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-23451011084548b7878248e13e6d5214
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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