Sodium Hydroxide → HCID 67442775, compound

HRID 1801375Notes

Reaction equation

HRID 1801375 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([CH:25]=[CH:26][CH:27]=1)[C:15]([O:17]CC1C=CC=CC=1)=[O:16])[C:6]([CH3:29])([CH3:28])[CH2:5]2.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([CH:25]=[CH:26][CH:27]=1)[C:15]([OH:17])=[O:16])[C:6]([CH3:29])([CH3:28])[CH2:5]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67442226HCID 67442226, compound

Product 1

HCID 67442775HCID 67442775, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzyl 3-(6-chloro-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoate (914 mg, 2.25 mmol) in methanol (30 mL) and aqueous sodium hydroxide solution (2 M, 17 mL, 34 mmol) was heated to reflux for 2 h. Solvent was removed under vacuum and the residue was acidified with 2N hydrochloric acid solution to pH=2. The precipitated white solid was collected to afford 539 mg of 3-(6-chloro-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoic acid (yield: 76%) as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. customSolvent was removed under vacuum
  4. customThe precipitated white solid was collected

Sources & evidence

ORD record
ord-123db0b53cb0470da41da8e23f05f077
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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