Methanol → HCID 178426048, compound

HRID 1501120Notes

Reaction equation

HRID 1501120 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3](=O)[CH2:4][C:5](=O)[CH3:6].[C:11](#[N:15])[CH2:12][C:13]#[N:14].C[OH:17]>>[OH:17][C:11]1[N:15]=[C:5]([CH3:6])[CH:4]=[C:3]([C:2]([F:10])([F:9])[F:1])[C:12]=1[C:13]#[N:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 8010MalononitrileHCID 739431,1,1-Trifluoro-2,4-pentanedione

Product 1

HCID 178426048HCID 178426048, compoundYield 40%

Procedure

To a solution of 1,1,1-trifluoropentane-2,4-dione (5.8 g, 37.7 mmol) in methanol (20 mL) was added malononitrile (5 g, 75 mmol) and then the mixture was heated to reflux. The mixture was maintained at the same temperature for 12 hours. The resultant mixture was cooled to room temperature, and then filtered. The solid was washed with methanol to give pure 2-hydroxy-6-methyl-4-(trifluoromethyl)nicotinonitrile (3 g, 40%). 1H NMR (300 MHz, d6-DMSO): δ 13.36 (s, 1H), 6.65 (s, 1H), 2.38 (s, 3H).

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureThe mixture was maintained at the same temperature for 12 hours
  3. filtrationfiltered
  4. washThe solid was washed with methanol

Sources & evidence

ORD record
ord-1fbe9f5604f8401488328216e84beba0
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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