Hydrochloric Acid → 2-Amino-1-(2,5-dimethoxyphenyl)ethan-1-ol

HRID 975937Notes

Reaction equation

HRID 975937 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]([OH:14])[C:12]#[N:13].B.Cl>C1COCC1>[NH2:13][CH2:12][CH:11]([C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[OH:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 12216529α-Hydroxy-2,5-dimethoxybenzeneacetonitrile

Product 1

HCID 432602-Amino-1-(2,5-dimethoxyphenyl)ethan-1-olYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.84 g (14.7 mmol) of (2, 5 dimethoxyphenyl)-hydroxy acetonitrile in 10 ml of dry THF was stirred and cooled using ice bath as a 1 M solution of borane in THF (90 mL) was added dropwise. After the addition was complete, the mixture was heated at reflux for 20 h. It was cooled and treated with 40 mL of 6N hydrochloric acid and washed with ethyl acetate. The aqueous layer was neutralized with 1N sodium hydroxide and extracted with ethyl acetate and concentrated to afford the desired compound as a white solid 1.5 g (52%). 1H NMR (300MHz, CDCl3) δ 6.97 (d, 1H, J=2.5 Hz), 6.73-6.69(m, 2H), 4.83-4.81(t, 1H, J=4.1 Hz), 3.72(s, 3H), 3.71(s, 3H), 2.89-2.65(m, 2H), 2.16(brs, 2H)

Workup

  1. temperaturecooled
  2. additionwas added dropwise
  3. additionAfter the addition
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 20 h
  6. temperatureIt was cooled
  7. washwashed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4965026ecec549299950638e6680434e
Source dataset
uspto-grants-1997_03
Patent number
US05610174

Reaction notes

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