Borane → 3-Aminobenzyl alcohol

HRID 1162195Notes

Reaction equation

HRID 1162195 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].B.[NH4+].[Cl-]>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6331BoraneHCID 74193-Aminobenzoic AcidHCID 25517Ammonium Chloride

Product 1

HCID 802933-Aminobenzyl alcoholYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino benzoic acid (1.05 g, 7.65 mmoles) was dissolved in THF (30 mL) under nitrogen atmosphere. Borane (BH3 1M solution in THF, 24 ml, 24 mmoles) was added, and the resulting solution was stirred at room temperature for 20 hours. The reaction mixture was then poured into a saturated NH4Cl solution (100 mL) and extracted with AcOEt (3×100 mL). The organic layer was dried over Na2SO4 and evaporated to dryness to yield 388 mg of the title compound, which was employed in the next step without further purification.

Workup

  1. extractionextracted with AcOEt (3×100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-04ea6657ddc44a0aabfaab6f4a25b601
Source dataset
uspto-grants-2010_10
Patent number
US07820698B2

Reaction notes

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