Sodium Hydroxide → HCID 58476206, compound

HRID 1801373Notes

Reaction equation

HRID 1801373 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:11][C:10]2[C:5](=[C:6]([C:12]([O:14]C)=[O:13])[CH:7]=[CH:8][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](=[C:6]([C:12]([OH:14])=[O:13])[CH:7]=[CH:8][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 67441324HCID 67441324, compound

Product 1

HCID 58476206HCID 58476206, compoundYield 38.2%

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-8-carboxylate (76 mg, 0.18 mmol) in methanol (2.7 mL) and sodium hydroxide aqueous solution (1M, 2.34 mL, 2.34 mmol) was heated to reflux for 1.5 h, LC-MS showed the reaction was complete. The solvent was removed in vacuo and the residue was acidified with 1M hydrochloric acid solution until lots of white solid precipitated, which was collected by filtration and washed with water, dried in vacuo to afford 28 mg of 3,3-dimethyl-2-(3-(1-methylpyrrolidin-3-ylcarbamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-8-carboxylic acid as a white solid. Yield: 38%. MS (ESI+APCI) M+1=408.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. customThe solvent was removed in vacuo
  4. customprecipitated
  5. filtrationwhich was collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1f79436840684ae997ddfcea9b219dc9
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…