Hydrochloric Acid → 2-Hydroxy-6-(trifluoromethyl)nicotinamide

HRID 658353

反応式

HRID 658353 の反応式
C[O-].[Na+].[CH2:4]([C:8]([NH2:10])=[O:9])[C:5]([NH2:7])=[O:6].C(O[CH:14]=[CH:15][C:16](=O)[C:17]([F:20])([F:19])[F:18])C.Cl>CO>[O:6]=[C:5]1[C:4]([C:8]([NH2:10])=[O:9])=[CH:14][CH:15]=[C:16]([C:17]([F:20])([F:19])[F:18])[NH:7]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7911MalonamideHCID 27803954-Ethoxy-1,1,1-trifluoro-3-buten-2-oneHCID 10942334Sodium Methoxide

生成物 1

HCID 27751142-Hydroxy-6-(trifluoromethyl)nicotinamide収率 83%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
45 °C

実験手順

Sodium methoxide (74 g, 1.37 mol) was dissolved in methanol (1,000 mL), and malon diamide (100 g, 0.979 mol) was added to this solution at room temperature. To this mixture, 4-ethoxy-1,1,1-trifluoro-3-buten-2-one (191 g, 1.14 mol) was added dropwise at a temperature between 25 and 30° C., and the resultant mixture was refluxed under heating for 2 hours. After cooling to 45° C., concentrated hydrochloric acid was added to the mixed solution to give a pH of 3 to 4, and 500 mL of methanol was distilled off at normal pressure. To the residue, water (500 mL) was added, and the mixture was stirred for a day at room temperature. The resultant product was precipitated while cooling with ice. Thus obtained crystal was collected by filtration, washed with water, and then dried under reduced pressure, to obtain 167 g of a subject compound (yield: 83%).

後処理

  1. temperatureunder heating for 2 hours
  2. distillationwas distilled off at normal pressure
  3. additionTo the residue, water (500 mL) was added
  4. customThe resultant product was precipitated
  5. temperaturewhile cooling with ice
  6. filtrationThus obtained crystal was collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure

出典と根拠

ORDレコード
ord-34c2b56aba994822b4ca63e566bea97d
出典データセット
uspto-grants-2011_12
特許番号
US08076487B2

関連ノート

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