Sodium Hydroxide → 2-(4-Chloro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 1801276Notes

Reaction equation

HRID 1801276 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22]C)=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[NH:24][C:25](=[O:29])[CH:26]([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67441325Methyl 2-(4-chloro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 534922532-(4-Chloro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 57.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(4-chloro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (216 mg, 0.52 mmol) in methanol (8 mL) and 4.2 mL of aqueous solution of sodium hydroxide (1 M, 4.2 mmol) was stirred at reflux for 2 h. Thin layer chromatography indicated that the starting material was consumed completely. Methanol was removed under reduced pressure and the residue was acidified to pH=6 with 1 M hydrochloric acid solution. The precipitated white solid were collected by filtration and dissolved in Ethyl acetate, dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford 120 mg of 2-(4-chloro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. LC-MS (M+1)=383.

Workup

  1. temperatureat reflux for 2 h
  2. customwas consumed completely
  3. customMethanol was removed under reduced pressure
  4. filtrationThe precipitated white solid were collected by filtration
  5. dissolutiondissolved in Ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4eddf8570fb94b5ba92daff59246cb70
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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