Lithium Hydroxide → 3-(2-Propylamino-4-trifluoromethyl-phenyl)-acrylic acid

HRID 1042448Notes

Reaction equation

HRID 1042448 reaction equation
C[O:2][C:3](=[O:20])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[NH:16][CH2:17][CH2:18][CH3:19].[Li+].[OH-]>C1COCC1.CO>[CH2:17]([NH:16][C:7]1[CH:8]=[C:9]([C:12]([F:13])([F:15])[F:14])[CH:10]=[CH:11][C:6]=1[CH:5]=[CH:4][C:3]([OH:20])=[O:2])[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 668555113-(2-Propylamino-4-trifluoromethyl-phenyl)-acrylic acid methyl ester

Product 1

HCID 668558653-(2-Propylamino-4-trifluoromethyl-phenyl)-acrylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

3-(2-Propylamino-4-trifluoromethyl-phenyl)-acrylic acid methyl ester (67.3 mg, 0.234 mmol) was reacted with aqueous 1N LiOH solution (5 ml) in THF/CH3OH (10 ml/5 ml) for 1 hr. The reaction solvent removed in vacuo. Water (30 ml) was added to the resulting residue, which was neutralized with 1N HCl solution, an then extracted with ethyl acetate (30 ml×3). The combined organic layer was dried over MgSO4 and concentrated in vacuo to yield title compound (55 mg, 0.201 mmol, 86%).

Workup

  1. customThe reaction solvent removed in vacuo
  2. additionWater (30 ml) was added to the resulting residue, which
  3. extractionan then extracted with ethyl acetate (30 ml×3)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-379c191dbacc485ba71d44999a74360f
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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