Hydrochloric Acid → HCID 58476246, compound

HRID 1801265Notes

Reaction equation

HRID 1801265 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[CH:8]=[C:9]([CH:13]2[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:25]([O:27]C)=[O:26])[CH:19]=3)[NH:14]2)[CH:10]=[CH:11][CH:12]=1)=[O:6])([CH3:3])[CH3:2].[OH-].[Na+].C(OCC)(=O)C.Cl>CO.O>[CH:1]([NH:4][C:5]([C:7]1[CH:8]=[C:9]([CH:13]2[C:22]([CH3:23])([CH3:24])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:25]([OH:27])=[O:26])[CH:19]=3)[NH:14]2)[CH:10]=[CH:11][CH:12]=1)=[O:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67443747HCID 67443747, compound

Product 1

HCID 58476246HCID 58476246, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-(3-(isopropylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (120 mg, 0.315 mmol) in methanol (4.8 mL) and 2N sodium hydroxide aqueous solution (3.2 mL, 6.4 mmol) was heated to reflux for 2 h. Thin layer chromatography (petroleum ether:ethyl acetate=3:1) and 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=6, extracted with ethyl acetate/tetrahydrofuran, washed with brine and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo gave 92 mg of 2-(3-(isopropylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. Yield: 80%. LC-MS (M+1)=367.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. customThe solvent was removed in vacuo
  4. customto give white solid, which
  5. extractionextracted with ethyl acetate/tetrahydrofuran
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-9ba89cb4ba494590ac1e0a2e91ade754
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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