Hydrochloric Acid → HCID 58476276, compound

HRID 1801300Notes

Reaction equation

HRID 1801300 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14]C)=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:25])[NH:23][CH3:24])[CH:17]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1([CH3:26])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([OH:14])=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:25])[NH:23][CH3:24])[CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67441787HCID 67441787, compound

Product 1

HCID 58476276HCID 58476276, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 3,3-dimethyl-2-(3-(methylcarbamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (85 mg, 0.24 mmol) in methanol (4.6 mL) and 1N sodium hydroxide aqueous solution (3.6 mL, 3.6 mmol) was heated to reflux for 1 h. LC-MS showed the reaction was complete. The solvent was removed in vacuo to give white solid, which was dissolved in water and acidified with 1N hydrochloric acid solution to pH=2. The precipitated white solid was collected by filtration and back-dissolved in aqueous sodium hydroxide solution, then was acidified with 1 M hydrochloric acid solution again to pH=7. The white precipitated solid was collected by filtration and dried in vacuo to afford 35 mg of 3,3-dimethyl-2-(3-(methyl carbamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid. Yield: 42.9%. LC-MS (M+1)=339.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. customThe solvent was removed in vacuo
  4. customto give white solid, which
  5. filtrationThe precipitated white solid was collected by filtration
  6. dissolutionback-dissolved in aqueous sodium hydroxide solution
  7. customThe white precipitated solid
  8. filtrationwas collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-29ddce2ecd764c609a59d611927ce718
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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