2-Amino-6-(trifluoromethyl)benzoic acid → HCID 54486842, compound

HRID 1056441Notes

Reaction equation

HRID 1056441 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:3]=1[C:4](O)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 27785082-Amino-6-(trifluoromethyl)benzoic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 54486842HCID 54486842, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-amino-6-(trifluoromethyl)benzoic acid (20 g, 97 mmol) was dissolved in tetrahydrofuran (120 mL) in a 3-neck RB flask equipped with an addition funnel and a condenser. The solution was cooled in an ice-water bath. LiAlH4 (83 mL, 166 mmol) (2M solution in THF) was then added dropwise. After all of the LiAlH4 solution was added, the reaction mixture was allowed to warm to room temperature and stirred at room temperature overnight. The reaction was then quenched by adding 10 mL of Water, then 10 mL of 15% NaOH and then 25 mL of Water. The salts were filtered off and the solvents were evaporated under vacuum. The product was used as is (18 g, 97% yield.

Workup

  1. customequipped with an addition funnel and a condenser
  2. temperatureThe solution was cooled in an ice-water bath
  3. customThe reaction was then quenched
  4. additionby adding 10 mL of Water
  5. filtrationThe salts were filtered off
  6. customthe solvents were evaporated under vacuum

Sources & evidence

ORD record
ord-d2c9abc313334f12b8b680d62f767f92
Source dataset
uspto-grants-2016_07
Patent number
US09397302B2

Reaction notes

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