Hydrochloric Acid → 3-Benzyloxy-5-hydroxybenzylamine

HRID 1174812Notes

Reaction equation

HRID 1174812 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.B.C1COCC1.Cl.C([O-])(O)=O.[Na+]>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 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 219043673-Benzyloxy-5-hydroxybenzonitrile

Product 1

HCID 219043653-Benzyloxy-5-hydroxybenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

Sources & evidence

ORD record
ord-94e460ef441d4cdf8ce4ed64d38f1538
Source dataset
uspto-grants-2010_11
Patent number
US07838542B2

Reaction notes

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