Hydrochloric Acid → 3-Hydroxy-alpha-((methylamino)methyl)benzenemethanol

HRID 20624Notes

Reaction equation

HRID 20624 reaction equation
Cl.COC[O:5][C:6]1[CH:7]=[C:8]([CH:12]([OH:16])[CH2:13][NH:14][CH3:15])[CH:9]=[CH:10][CH:11]=1>CO>[OH:16][CH:12]([C:8]1[CH:7]=[C:6]([OH:5])[CH:11]=[CH:10][CH:9]=1)[CH2:13][NH:14][CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 593480531-(3-Methoxymethoxy-phenyl)-2-methylamino-ethanol

Product 1

HCID 47823-Hydroxy-alpha-((methylamino)methyl)benzenemethanolYield 67.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (0.1 mL) was added to 1-(3-methoxymethoxy-phenyl)-2-methylamino-ethanol (300 mg, 1.42 mmol) dissolved in methanol (3 mL). The resulting mixture was heated at reflux for about 30 minutes, and then cooled to ambient temperature. The mixture was concentrated to dryness, and the residue was purified by flash column chromatography on silica gel (1×16 cm, dichloromethane/methanol/ammonium hydroxide=45/8/1 elution) to give the title compound (160 mg, 67%). 1H NMR (300 MHz, CD3OD) δ 7.14 (t, 1H, J=8.1 Hz), 6.81-6.80 (m, 2H), 6.69-6.66 (m, 1H), 4.71-4.67 (m, 1H), 2.78-2.66 (m, 2H), 2.41 (s, 3H); LC-MS: m/z=168 (MH)+; HPLC: 98% (Purity).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for about 30 minutes
  3. concentrationThe mixture was concentrated to dryness
  4. customthe residue was purified by flash column chromatography on silica gel (1×16 cm, dichloromethane/methanol/ammonium hydroxide=45/8/1 elution)

Sources & evidence

ORD record
ord-64f2638309c3495d894c6a60ff1f0374
Source dataset
uspto-grants-2010_06
Patent number
US07745665B2

Reaction notes

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