Pyridine → 2-Amino-6-chloropyridine-3-carbonitrile

HRID 444831

反応式

HRID 444831 の反応式
Cl.[NH2:2][C:3]1[C:8]([CH:9]=[N:10]O)=[CH:7][CH:6]=[C:5]([Cl:12])[N:4]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[NH2:2][C:3]1[C:8]([C:9]#[N:10])=[CH:7][CH:6]=[C:5]([Cl:12])[N:4]=1

参加物

7

反応物 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 866350212-Amino-6-chloropyridine-3-carbaldehyde oxime hydrochloride

生成物 1

HCID 203116862-Amino-6-chloropyridine-3-carbonitrile

試薬・触媒・溶媒 3

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

11.15 g (53.6 mmol) of 2-amino-6-chloropyridine-3-carbaldehyde oxime hydrochloride (Example 27A) were initially charged in dioxane, 13 ml (161 mmol) of pyridine were added and the mixture was cooled to 0° C. 8.3 ml (58.95 mmol) of trifluoroacetic anhydride were added, and the reaction was warmed to RT and then stirred at 60° C. for 2 h. The reaction mixture was taken up in a mixture of ethyl acetate and sodium bicarbonate solution. The organic phase was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated on a rotary evaporator. The residue was suspended in dichloromethane:diethyl ether 3:1, and the solid was filtered off with suction and dried. This gave 5.56 g (66% of theory) of the product as a solid.

後処理

  1. temperaturethe reaction was warmed to RT
  2. washThe organic phase was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. filtrationthe solid was filtered off with suction
  6. customdried

出典と根拠

ORDレコード
ord-b64671c2b5694f00acfa2cdc97cdcd23
出典データセット
uspto-grants-2013_07
特許番号
US08476267B2

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