Hydrochloric Acid → 3-Benzyloxy-5-hydroxybenzylamine

HRID 500418Notes

Reaction equation

HRID 500418 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([OH:17])[CH:16]=1)[C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1.B.C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([OH:17])[CH:16]=1)[CH2:12][NH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 219043673-Benzyloxy-5-hydroxybenzonitrile

Product 1

HCID 219043653-Benzyloxy-5-hydroxybenzylamine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2723981Borane;tetrahydrofuranSolvent

Procedure

3-benzyloxy-5-hydroxybenzonitrile (225 mg, 1 mmol) was dissolved in 2 mL THF 2 mL of BH3-THF (1.5 M in THF and ether) was added dropwise, then the mixture was heated at reflux temperature for 3 hours. After cooling, the mixture was carefully poured to 3M HCl (ice cooled) and allowed to stir for 20 hours at room temperature. The mixture was neutralized with solid NaHCO3, thus the product precipitated as a white solid. The product was collected by filtration, washed with water, and dried (140 mg, 61%): MP 164-166° C. (dec); 1H NMR (DMSO-d6, 400 MHz) δ 9.28 (br, 1H), 7.41 (d, 2H, J=6.9 Hz), 7.36 (dd, 2H, J=7.0 and 7.6 Hz), 7.30 (dd, 1H, J=7.0 and 6.6 Hz), 6.43 (s, 1H), 6.32 (s, 1H), 6.21 (dd, 1H, J=2.2 and 2.0 Hz), 4.99 (S, 2H), 3.57 (S, 2H).

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture was heated
  3. temperatureat reflux temperature for 3 hours
  4. temperatureAfter cooling
  5. customthus the product precipitated as a white solid
  6. filtrationThe product was collected by filtration
  7. washwashed with water
  8. customdried (140 mg, 61%)

Sources & evidence

ORD record
ord-328efd5108e14930a4b0fb22827cf48a
Source dataset
uspto-grants-2010_08
Patent number
US07772216B2

Reaction notes

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