Potassium Hydroxide → 3-Amino-α,α-dimethylbenzenemethanol

HRID 1994119Notes

Reaction equation

HRID 1994119 reaction equation
Cl.NO.[OH-].[K+].CC1[N:8]([C:13]2[CH:14]=[C:15]([C:19]([OH:22])([CH3:21])[CH3:20])[CH:16]=[CH:17][CH:18]=2)C(C)=CC=1>C(O)C.O>[NH2:8][C:13]1[CH:14]=[C:15]([C:19]([OH:22])([CH3:20])[CH3:21])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 58674658HCID 58674658, compound

Product 1

HCID 102612643-Amino-α,α-dimethylbenzenemethanolYield 99.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of hydroxylamine hydrochloride (7.42 g, 107 mmol) and potassium hydroxide (5.41 g, 82.0 mmol) in ethanol (65 mL) and water (30 mL) was added 2-[3-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]propan-2-ol (0.840 g, 3.66 mmol). The heterogeneous mixture was heated at 120° C. overnight and then concentrated. The residue was purified by column chromatography to give the desired product (0.55 g, 65%). 1H NMR (400 MHz, CDCl3) δ: 7.11-7.15 (m, 1H), 6.85-6.87 (m, 1H), 6.84 (ddd, 1H), 6.58 (ddd, 1H), and 1.55 (s, 6H). LCMS: (FA) ES+ 152.0 (M+1).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0e49db5822374cfb912200101e761a22
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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