2-(3,4-Dimethylphenyl)acetonitrile → 2-(3,4-dimethylphenyl)-N'-hydroxyethanimidamide

HRID 330250

Reaction equation

HRID 330250 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[CH3:8].Cl.[NH2:13][OH:14].C[O-].[Na+].CO>CO>[OH:14][N:13]=[C:10]([NH2:11])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 3

HCID 764012-(3,4-Dimethylphenyl)acetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 23694274Sodium methanolate methanol

Product 1

HCID 51878672-(3,4-dimethylphenyl)-N'-hydroxyethanimidamideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,4-Dimethylphenylacetonitrile (10 g, 0.069 mol) was added to a mixture of hydroxylamine hydrochloride (9.57 g, 0.14 mol), methanol (100 mL) and 25% sodium methoxide/methanol (31.5 mL, 0.14 mol) at room temperature. After stirring for 16 hours at room temperature, the reaction mixture was concentrated in vacuo. The resultant oil was partitioned between methylene chloride and water. The organic phase was separated, washed with water, dried over magnesium sulfate and concentrated in vacuo to yield the desired product (11.4 g, 93%) as a white solid. Recrystallization from toluene afforded an analytical sample m.p. 59°-60° C.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe resultant oil was partitioned between methylene chloride and water
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2151eb6996b04815873593e7d1dea55c
Source dataset
uspto-grants-1990_01
Patent number
US04895862

Linked notes

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