2-Amino-6-fluorobenzoic acid → (2-Amino-6-fluorophenyl)methanol

HRID 1485986Notes

Reaction equation

HRID 1485986 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:9]=1[C:10](O)=[O:11]>C1COCC1>[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:9]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 5211422-Amino-6-fluorobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11521092(2-Amino-6-fluorophenyl)methanolYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (987 mg, 26 mmol) was added slowly to a solution of 2-amino-6-fluoro-benzoic acid (2.69 g, 17.3 mmol) in dry THF (20 mL) at 0° C. The mixture was stirred at room temperature for approximately 1 hr and cooled to 0° C. again. Na2SO4.10H2O (10 g) was added slowly with stirring for 20 minutes. The mixture was filtered, the solid was washed with THF. The solution was concentrated to yield a yellow solid as (2-amino-6-fluoro-phenyl)-methanol (2.49 g). MS [M-OH]+: 124.1; tR=0.57 min. (method 1)

Workup

  1. temperaturecooled to 0° C. again
  2. stirringwith stirring for 20 minutes
  3. filtrationThe mixture was filtered
  4. washthe solid was washed with THF
  5. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-7e70dd900616485b88807ce18d426ea0
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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