2-Amino-6-methyl-4-oxo-4H-pyran-3-carbonitrile → HCID 178429083, compound

HRID 1500966Notes

Reaction equation

HRID 1500966 reaction equation
[NH2:1][C:2]1[O:3][C:4]([CH3:11])=[CH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9]>Cl>[OH:3][C:2]1[N:1]=[C:4]([CH3:11])[CH:5]=[C:6]([OH:10])[C:7]=1[C:8]#[N:9]

Participants

3

Reactant 1

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

Product 1

HCID 178429083HCID 178429083, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 2-amino-6-methyl-4-oxo-4H-pyran-3-carbonitrile (6.0 g, 40 mmol) in 10% hydrochloride acid (60 mL) was heated under reflux for 4 hours. The precipitate was collected by filtration and washed with water, and then recrystallized from methanol to give 2,4-dihydroxy-6-methylnicotinonitrile (5.0 g, 83%) as a brown solid. 1H NMR (300 MHz, CD3OD): δ 12.46-12.44 (m, 1H), 11.69 (s, 1H), 5.85 (s, 1H), 2.15 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e1e961221b944bde917f83a106368fea
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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