Dimethylformamide → 6-Aminopicolinonitrile

HRID 2169999ノート

反応式

HRID 2169999 の反応式
Br[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[CH3:15][N:16](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:8][C:6]1[N:7]=[C:2]([C:15]#[N:16])[CH:3]=[CH:4][CH:5]=1

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 3008092-Amino-6-bromopyridine

生成物 1

HCID 5642986-Aminopicolinonitrile

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
170 °C

実験手順

340 mg (2.89 mmol, 1 eq) of zinc cyanide are added to 500 mg (2.89 mmol, 1 eq) of 6-bromopyridin-2-ylamine in 10 ml of dimethylformamide in a microwave tube. 170 mg (0.147 mmol, 0.05 eq) of tetrakis(triphenylphosphine)palladium are added. The medium is heated at 170° C. for 1 hour 30 minutes in a microwave oven. 50 ml of ethyl acetate are added to the medium, which is filtered over celite. The filtrate is washed with water and extracted with ethyl acetate. The organic phases are combined and dried over sodium sulphate. The residue is triturated in heptane. 6-Aminopyridine-2-carbonitrile is obtained in the form of an orange solid.

後処理

  1. filtrationis filtered over celite
  2. washThe filtrate is washed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customThe residue is triturated in heptane

出典と根拠

ORDレコード
ord-ca3e6d5242184798b09a0a4dbc81f5ce
出典データセット
uspto-grants-2015_06
特許番号
US09050266B2

反応ノート

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