Sodium Hydroxide → HCID 67441589, compound

HRID 1801346Notes

Reaction equation

HRID 1801346 reaction equation
[CH:1]1([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]3[C:26]([CH3:28])([CH3:27])[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:29]([O:31]C)=[O:30])[CH:23]=4)[NH:18]3)[CH:13]=[CH:14][C:15]=2[F:16])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]3[C:26]([CH3:28])([CH3:27])[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:29]([OH:31])=[O:30])[CH:23]=4)[NH:18]3)[CH:13]=[CH:14][C:15]=2[F:16])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67441477HCID 67441477, compound

Product 1

HCID 67441589HCID 67441589, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(3-(cyclohexanecarboxamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (0.26 mmol, 1.0 eq.) and 4.5 mL sodium hydroxide (1 mol/L) in 3 mL methanol was stirred at reflux for 1-2 h. LC-MS indicated that the starting material was consumed completely. The methanol was removed by reduced pressure. The residue was acidified pH to 5-6 with 1 M hydrochloric acid. A lot of precipitates were formed and collected by filtration to afford 2-(3-(cyclohexanecarboxamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid; Yield: 74%; MS (ESI+APCI) M−1=423.

Workup

  1. temperatureat reflux for 1-2 h
  2. customwas consumed completely
  3. customThe methanol was removed by reduced pressure
  4. customA lot of precipitates
  5. customwere formed
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e5f73be15bef4148b87a236a58509c09
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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