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

HRID 1526962Notes

Reaction equation

HRID 1526962 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].[CH2:8]=[C:9]1[O:13][C:11](=[O:12])[CH2:10]1.Cl>O1CCCC1>[NH2:4][C:3]1[O:13][C:9]([CH3:8])=[CH:10][C:11](=[O:12])[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-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of malononitrile (3.3 g, 50 mmol) in anhydrous tetrahydrofuran (100 mL) was added sodium hydride (60% w/w, 2.2 g, 55 mmol) at −10° C. The resultant mixture was stirred for 2 hours. Then diketene (4.2 g, 50 mmol) was added dropwise to the solution. The mixture was allowed to warm to room temperature and continued stirring for 30 minutes. The mixture was neutralized with hydrochloric acid and then concentrated in vacuo to give crude 2-amino-6-methyl-4-oxo-4H-pyran-3-carbonitrile (6.0 g, 80%) as a red solid, which was used in the next step without further purification.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-353d3b4cddc649bb91649d1f14a7be23
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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