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

HRID 1501265Notes

Reaction equation

HRID 1501265 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-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of malononitrile (3.3 g, 50 mmol) in 100 ml of anhydrous tetrahydrofuran was added sodium hydride (60%, 2.2 g, 55 mmol) at −10° C. The resulting reaction mixture was stirred for 2 hours. Then diketene (4.2 g, 50 mmol) was added dropwise to the solution. The reaction mixture was allowed to warm to room temperature and continued to stir for 30 minutes. The mixture was neutralized with hydrochloric acid, and then concentrated to give crude product as red solid, which was used in the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. stirringto stir for 30 minutes
  3. concentrationconcentrated
  4. customto give crude product as red solid, which
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-abba68ae478945f39d9260bfa1a39571
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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