Hydrochloric Acid → 2-Amino-6-methyl-4-oxo-4H-pyran-3-carbonitrile

HRID 2206606Notes

Reaction equation

HRID 2206606 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].[CH2:8]=[C:9]1[O:12][C:11](=[O:13])[CH2:10]1.Cl>C1COCC1>[NH2:4][C:3]1[O:12][C:9]([CH3:8])=[CH:10][C:11](=[O:13])[C:2]=1[C:1]#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 12661DiketeneHCID 24758Sodium hydride

Product 1

HCID 114805352-Amino-6-methyl-4-oxo-4H-pyran-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Malononitrile (110 g, 1.67 mol) was dissolved in dry THF (1000 ml) and cooled in ice-water bath. NaH (60% in mineral oil, 67 g, 1.67 mol) was added portionwise below 10° C. very carefully while the reaction flash was evacuated with N2 flow. After addition completed, the mixture was stirred at 0° C. for 30 min. Then 4-methyleneoxetan-2-one (140 g, 1.67 mol) was added dropwise below 0° C. After addition completed, the mixture was stirred at −10° C. for 1H. The reaction mixture was neutralized by 4 N HCl and concentrated under vacuum to give compound 2-amino-6-methyl-4-oxo-4H-pyran-3-carbonitrile as an orange oil. The crude product was used to next step without further purification.

Workup

  1. customwas evacuated with N2 flow
  2. additionAfter addition
  3. additionAfter addition
  4. stirringthe mixture was stirred at −10° C. for 1H
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7f33eea49b2545b095daa45e00bd39c1
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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