Water → HCID 59497457, compound

HRID 1747468Notes

Reaction equation

HRID 1747468 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:11][C:12]([F:13])([F:14])[F:15]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27359514-amino-3-(trifluoromethoxy)benzoic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 59497457HCID 59497457, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

4-Amino-3-(trifluoromethoxy)benzoic acid 2.0 g (9.04 mmol) is dissolved in 50 mL of THF. Lithium aluminium hydride (1.4 g, 36.2 mmol) is added portionwise over 10 minutes. A reflux condensor is attached and the reaction mixture is refluxed for 6 h at 80° C. It is cooled to room temperature and the Fieser work up is performed (1.4 mL of water, 1.4 mL 15% NaOH, 4.2 mL of water). The granular inorganic precipitate is filtered and washed with THF. The organic fractions is combined and dried over anhydrous Na2SO4. The solvent is evaporated and the residue is purified on silica, eluting with 0-10% methanol/dichloromethane to give the title compound (1.2 g, 5.79 mmol 64%). (ESMS): ink 208.3 (M+H+).

Workup

  1. temperatureIt is cooled to room temperature
  2. filtrationThe granular inorganic precipitate is filtered
  3. washwashed with THF
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent is evaporated
  6. customthe residue is purified on silica
  7. washeluting with 0-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-a25dd39948454e2a8d7dbb5b369cd3f6
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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