Potassium Hydroxide → HCID 11451785, compound

HRID 1791879Notes

Reaction equation

HRID 1791879 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[O:5])[CH2:3][CH2:2]1.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br.[OH-].[K+]>CC(C)=O>[CH:1]1([C:4]([NH:6][C:7]2[CH:15]=[CH:14][C:13]([O:16][CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[C:18]([F:17])([F:27])[F:28])=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 728466HCID 728466, compound

Product 1

HCID 11451785HCID 11451785, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(cyclopropanecarbonyl-amino)-5-hydroxy-benzoic acid (7.0 g, 32 mmol) and 2-(trifluoromethyl)-benzyl bromide (9.09 g, 38 mmol) in 0.5 M KOH (158 mL, 79 mmol) and acetone (200 mL) was heated to reflux. After 4 hours, acetone was evaporated and the resulting mixture was diluted with more water and washed with CH2Cl2. The water phase was acidified with 1 M HCl and the resulting solid was collected by filtration. Recrystallisation in methanol gave the product as an off-white powder (6.0 g, yield 50%).

Workup

  1. temperaturewas heated to reflux
  2. customacetone was evaporated
  3. additionthe resulting mixture was diluted with more water
  4. washwashed with CH2Cl2
  5. filtrationthe resulting solid was collected by filtration
  6. customRecrystallisation in methanol

Sources & evidence

ORD record
ord-0b8091968c0248508f09ffdb2d46031b
Source dataset
uspto-grants-2006_07
Patent number
US07074831B2

Reaction notes

Loading…