Dimethylformamide → 3-Chloro-5-hydroxypicolinonitrile

HRID 2196370노트

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HRID 2196370 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([O:9]C(=O)C)[CH:5]=[N:6][C:7]=1Cl.[CH3:13][N:14](C=O)C>CC(OC)(C)C.O.[Ar].[Zn].[C-]#N.[C-]#N.[Zn+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].Cl[Pd]Cl>[Cl:1][C:2]1[C:7]([C:13]#[N:14])=[N:6][CH:5]=[C:4]([OH:9])[CH:3]=1

참가 물질

8

반응물 2

HCID 6228DimethylformamideHCID 145952225,6-Dichloropyridin-3-yl acetate

생성물 1

HCID 666654733-Chloro-5-hydroxypicolinonitrile

시약·촉매·용매 5

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 85978949argon Zn촉매HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
150 °C

실험 절차

To a solution of acetic acid 5,6-dichloro-pyridin-3-yl ester (CA 110861-18-2, Synthesis, 1990, 499) (4.88 g, 23.6 mmol) in anhydrous DMF (45 ml) was added after degasing with argon Zn-dust (70 mg, 1.07 mmol), Zn(CN)2 (1.28 g, 10.9 mmol) and DPPF PdCl2 (966 mg, 1.18 mmol) and the reaction mixture was heated for 6 h at 130° C. and 18 h at 150° C. The reaction mixture was diluted with TBME and H2O, filtered over Celite, and the product was extracted with TBME. Combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated. The title compound was obtained as a beige solid after crystallization from EtOAc-hexane: TLC (CH2Cl2-MeOH 19:1): Rf=0.22;

후처리

  1. filtrationfiltered over Celite
  2. extractionthe product was extracted with TBME
  3. washCombined extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f80c641d489e466ca62a113548426d70
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338413B1

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