Sodium Hydroxide → HCID 58476167, compound

HRID 1801256Notes

Reaction equation

HRID 1801256 reaction equation
[CH3:1][C:2]1([CH3:31])[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:30])[NH:23][CH:24]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25]2)[CH:17]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1([CH3:31])[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:30])[NH:23][CH:24]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25]2)[CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67441025HCID 67441025, compound

Product 1

HCID 58476167HCID 58476167, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3,3-dimethyl-2-(3-(1-methylpyrrolidin-3-ylcarbamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (150 mg, 0.36 mmol) in methanol (6 mL) and 1N sodium hydroxide aqueous solution (5.3 mL, 5.3 mmol) was heated to reflux for 4 h, LC-MS showed the reaction was complete. The solvent was removed in vacuo and the residual was acidified with 1N hydrochloric acid solution to pH=6. The precipitated white solid was collected by filtration and washed with acetone, dichloromethane and ether sequentially to afford 78 mg of 3,3-dimethyl-2-(3-(1-methylpyrrolidin-3-ylcarbamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. Yield: 53.8%, LC-MS (M+1)=408.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customThe solvent was removed in vacuo
  4. filtrationThe precipitated white solid was collected by filtration
  5. washwashed with acetone, dichloromethane and ether sequentially

Sources & evidence

ORD record
ord-516cce58d5634cb8b57b88bbeff5cfae
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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