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

HRID 1801267Notes

Reaction equation

HRID 1801267 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([NH:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[CH:16]=1)[C:9]([CH3:29])([CH3:28])[CH2:8]2)=[O:4].[OH-].[Na+]>CO.O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH:10]2[C:9]([CH3:28])([CH3:29])[CH2:8][C:7]3[C:12](=[CH:13][CH:14]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=3)[NH:11]2)=[CH:16][C:17]=1[NH:22][C:23](=[O:27])[CH:24]([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67441749Methyl-2-(4-fluoro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 674405182-(4-Fluoro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of methyl-2-(4-fluoro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (183 mg, 0.46 mmol), sodium hydroxide (312 mg, 7.8 mmol) in methanol/water (10 mL/4 mL) was heated to reflux for 1.5 h. LC-MS indicated that the starting material was consumed completely. The solvent was removed in vacuo and the residue was acidified with 2M hydrochloric acid solution to Ph=5. The precipitated white solid was collected by filtration and dissolved in acetone, dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give 2-(4-fluoro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid, which was purified by recrystallization from dichloromethane/methanol/Hexant to afford 140 mg of off-white crystal. Yield: 79.3%. LC-MS (M+1)=385.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. customwas consumed completely
  4. customThe solvent was removed in vacuo
  5. filtrationThe precipitated white solid was collected by filtration
  6. dissolutiondissolved in acetone
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3321f627943a45aaa351b7659af08d1d
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…