3-Cyanobenzoic acid → [3-(Aminomethyl)phenyl]methanol

HRID 1169558Notes

Reaction equation

HRID 1169558 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7])#[N:2].B.O1CCCC1>O1CCCC1>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][OH:7]

Participants

4

Reactant 2

HCID 158753-Cyanobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 21880609[3-(Aminomethyl)phenyl]methanolYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 20 g sample of 3-cyanobenzoic acid (12) (136 mmol) was suspended in 100 mL of dry tetrahydrofuran (THF). Borane-tetrahydrofuran complex (400 mL of 1.0 M solution in THF) was added dropwise over one hour and then stirred for an additional 3 hours. The reaction was quenched with 220 mL of concentrated HCl:water (1:1) to cleave the borane-alcohol complex. The THF was then evaporated off under vacuum. Solid NaOH pellets, 70 g total, were added slowly to neutralize the acid and bring the pH of the solution to 12. The aqueous phase was then extracted 4 times with 500 mL portions of ether. The ether extract was dried over MgSO4 and evaporated under vacuum to give 18 g (131 mmol) of 3-(aminomethyl)benzyl alcohol (13) as a light colored oil. 1H NMR (CDCl3/TMS) δ=1.95 (broad s, 3H, —OH and —NH2, exchangeable with D2O), 3.86 (s, 2H, —CH2—NH2), 4.66 (s, 2H, —CH2—OH), 7.27 (m, 4H, aromatic).

Workup

  1. customThe reaction was quenched with 220 mL of concentrated HCl:water (1:1)
  2. customThe THF was then evaporated off under vacuum
  3. additionSolid NaOH pellets, 70 g total, were added slowly
  4. extractionThe aqueous phase was then extracted 4 times with 500 mL portions of ether
  5. extractionThe ether extract
  6. dry with materialwas dried over MgSO4
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-f577825c3c774780a8d40b50b830a2c3
Source dataset
uspto-grants-2010_11
Patent number
US07825096B2

Reaction notes

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