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

HRID 1801297Notes

Reaction equation

HRID 1801297 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[C:25]([CH3:27])([CH3:26])[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:28]([O:30]C)=[O:29])[CH:22]=3)[NH:17]2)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[C:25]([CH3:27])([CH3:26])[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:28]([OH:30])=[O:29])[CH:22]=3)[NH:17]2)=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67442804HCID 67442804, compound

Product 1

HCID 584762542-(4-Benzamidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(4-benzamidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (67 mg, 0.16 mmol) in methanol (8 mL) and aqueous sodium hydroxide solution (1 M, 1.2 mL, 1.2 mmol) was heated to reflux for 5 h, LC-MS showed the reaction was complete. The solvent was removed in vacuo and the residue was acidified with 2 M hydrochloric acid solution until lots of yellow solid precipitated, which was collected by filtration to afford 51 mg of 2-(4-benzamidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid in 80% yield. MS (ESI+APCI) M+1=401.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. customThe solvent was removed in vacuo
  4. customprecipitated
  5. filtrationwhich was collected by filtration

Sources & evidence

ORD record
ord-1ccb85c04e6a4dd39e9596384ac98120
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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