Sodium Hydroxide → HCID 67441188, compound

HRID 1801317Notes

Reaction equation

HRID 1801317 reaction equation
[CH:1]1([C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]3[C:25]([CH3:27])([CH3:26])[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:28]([O:30]C)=[O:29])[CH:22]=4)[NH:17]3)[CH:12]=[CH:13][C:14]=2[F:15])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]3[C:25]([CH3:27])([CH3:26])[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:28]([OH:30])=[O:29])[CH:22]=4)[NH:17]3)[CH:12]=[CH:13][C:14]=2[F:15])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67439957HCID 67439957, compound

Product 1

HCID 67441188HCID 67441188, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(3-(cyclopentanecarboxamido)-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-(cyclopentanecarboxamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid; Yield: 70%; MS (ESI+APCI) M+1=411.

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-e4ce325c4a0c4da78ff3cc4688e14706
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…