Borohydride → (2-Amino-4-methoxyphenyl)methanol

HRID 524070

Reaction equation

HRID 524070 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[BH4-]>C1COCC1>[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 28123BorohydrideHCID 3510102-Amino-4-methoxybenzoic acid

Product 1

HCID 45090899(2-Amino-4-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-amino-4-methoxybenzoic acid (15.0 g, 89.8 mmol) in THF (300 mL) was added borohydride in THF (450 mL, 450 mmol) at 0° C., and the reaction mixture was stirred at RT overnight. LCMS showed the reaction was completed. The reaction was quenched with water (150 mL) and extracted with ethyl acetate (500 mL×3). The organic layers were separated, combined, washed with water (200 mL) and brine (200 mL), dried over sodium sulfate, filtered and concentrated to afford the title compound. MS (ES+) C8H11NO2 requires: 153. found: 154 [M+H]+.

Workup

  1. customThe reaction was quenched with water (150 mL)
  2. extractionextracted with ethyl acetate (500 mL×3)
  3. customThe organic layers were separated
  4. washwashed with water (200 mL) and brine (200 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7f05f344974642fb9b518b15511e2729
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Linked notes

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