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

HRID 2045585Notes

Reaction equation

HRID 2045585 reaction equation
[Cl:1][C:2]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:14]2[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]([O:28]C)=[O:27])[CH:20]=3)[NH:15]2)[CH:10]=[CH:11][C:12]=1[F:13])=[O:5].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:14]2[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]([OH:28])=[O:27])[CH:20]=3)[NH:15]2)[CH:10]=[CH:11][C:12]=1[F:13])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67440538Methyl 2-(3-(2-chloro-4-fluorobenzamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 674407332-(3-(2-Chloro-4-fluorobenzamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(3-(2-chloro-4-fluorobenzamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (100 mg, 0.2 mmol), 3.1 mL aqueous solution of sodium hydroxide (124 mg, 3.1 mmol) in 5 mL methanol was stirred at reflux for 1 h. LC-MS indicated that the starting material was consumed completely. The solvent was removed by reduced pressure. The residue was purified by column chromatography (petroleum ether/ethyl acetate=1:1) to afford 68 mg of 2-(3-(2-chloro-4-fluorobenzamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a pale yellow solid; yield: 72.3%. MS (ESI+APCI) M+1=471.

Workup

  1. temperatureat reflux for 1 h
  2. customwas consumed completely
  3. customThe solvent was removed by reduced pressure
  4. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-74648b02f5b24917ba7c46e2184a230a
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

Loading…