Malononitrile → 2-AMINO-4-METHYL-3-FURONITRILE

HRID 1992306Notes

Reaction equation

HRID 1992306 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH3:6][C:7]([CH2:9][OH:10])=O.C(N(CC)CC)C>CO>[NH2:4][C:3]1[O:10][CH:9]=[C:7]([CH3:6])[C:2]=1[C:1]#[N:5]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8299HydroxyacetoneHCID 8471Triethylamine

Product 1

HCID 110188532-AMINO-4-METHYL-3-FURONITRILEYield 30.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of malononitrile (0.96 g, 14.6 mmol), acetol (1.08 g, 14.6 mmol) in methanol (10 mL) at 0° C. was added, dropwise, triethylamine (2.0 mL). The reaction mixture was stirred at room temperature overnight. After removal of solvent under reduced pressure the crude solid washed with cold isopropanol to give product as white powder (0.54 g, 30%). HPLC/MS: (M+H)+ 123.3 m/z. Retention time (LC-MS)=1.81 min. 1H NMR (CD3OD): 6.58(s, 1H,); 1.95 (s, 3H).

Workup

  1. additionwas added
  2. customAfter removal of solvent under reduced pressure the crude solid
  3. washwashed with cold isopropanol

Sources & evidence

ORD record
ord-8718c6332dd441c4b3529492a6e8d53c
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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