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

HRID 1501259Notes

Reaction equation

HRID 1501259 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 anhydrous tetrahydrofuran (100 mL) 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 warmed to room temperature and continued to stir for 30 minutes. The mixture was neutralized with hydrochloric acid, and then concentrated in vacuo 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 in vacuo
  4. customto give crude product as red solid, which
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-6375d35d2162482288e00c0bda8fb246
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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