Sodium Hydroxide → HCID 53492321, compound

HRID 1801341Notes

Reaction equation

HRID 1801341 reaction equation
[CH3:1][C:2]1([CH3:30])[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:29])[NH:23][CH:24]2[CH2:27][N:26]([CH3:28])[CH2:25]2)[CH:17]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1([CH3:30])[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:29])[NH:23][CH:24]2[CH2:25][N:26]([CH3:28])[CH2:27]2)[CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67443220HCID 67443220, compound

Product 1

HCID 53492321HCID 53492321, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3,3-dimethyl-2-(3-(1-methylazetidin-3-ylcarbamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (100 mg, 0.25 mmol) in methanol (3.75 mL) and 1M sodium hydroxide aqueous solution (2.94 mL, 2.94 mmol) was heated to reflux for 1.5 h, LC-MS showed the reaction was complete and only the desired product formed. The solvent was concentrate in vacuo and the residue was dissolved in water and acidified with 1 M hydrochloric acid solution. The white precipitated solid was collected by filtration to afford 59 mg of 3,3-dimethyl-2-(3-(1-methylazetidin-3-ylcarbamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid was a white solid. Yield: 61.4%. MS (ESI+APCI) M+1=394.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h

Sources & evidence

ORD record
ord-6d2ab75389ed488aab16a19c08e87288
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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