2-Amino-6-chlorobenzoic acid → (2-Amino-6-chlorophenyl)methanol

HRID 2425757Notes

Reaction equation

HRID 2425757 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[C:10](O)=[O:11]>O1CCCC1>[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 750712-Amino-6-chlorobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 21925574(2-Amino-6-chlorophenyl)methanolYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (1.1 g, 29.1 mmol) in tetrahydrofuran (150 mL) was added 2-amino-6-chlorobenzoic acid (5 g, 29.1 mmol) at 0° C. The mixture was stirred at room temperature for 16 h. Then, the reaction mixture was quenched with sodium sulfate decahydrate (3 g) and brine (10 ml) and filtrated through a pad of Celite. The organic layer was concentrated in vacuo and the residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:2) to give 2.4 g (52%) of the title compound as a colorless oil.

Workup

  1. customThen, the reaction mixture was quenched with sodium sulfate decahydrate (3 g) and brine (10 ml)
  2. filtrationfiltrated through a pad of Celite
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-fdafb41236564ac5a86686c0b8c23b92
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

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