Acetone → (2-Amino-3-methyl-phenoxy)-acetonitrile

HRID 1687595Notes

Reaction equation

[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].Cl[CH2:11][C:12]#[N:13].C([O-])([O-])=O.[K+].[K+].CC(C)=O>>[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:11][C:12]#[N:13]

Participants

Reactant 4

HCID 180Acetone

HCID 7856Chloroacetonitrile

HCID 11430Potassium Carbonate

HCID 30141382-Amino-m-cresol

Product 1

HCID 43438079(2-Amino-3-methyl-phenoxy)-acetonitrileYield 51%

Conditions

Temperature: 50 °C

Procedure

Into a 1-Neck round-bottom flask was added 2-Amino-3-methyl-phenol (1.00 g, 0.00812 mol), Chloroacetonitrile (0.617 mL, 0.00974 mol), K2CO3 (1.35 g, 9.7 mmol), and Acetone (15 mL, 0.20 mol). The reaction mixture was heated at 50° C. for 4 hr, filtered and concentrated to afford title product (670 mg, 51%) LCMS 163 (M+H).

Workup

filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1bababa31e884d1e9eedca0813346a54
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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