Dimethylformamide → 6-Aminopicolinonitrile

HRID 2169999노트

반응식

HRID 2169999 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 5642986-Aminopicolinonitrile

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

반응 조건

온도
170 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ca3e6d5242184798b09a0a4dbc81f5ce
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050266B2

반응 노트

불러오는 중…