4-Aminonicotinaldehyde → 2-(2,6-dichloro-3-nitro-phenyl)-N-(3-formyl-pyridin-4-yl)-acetamide

HRID 270693

반응식

HRID 270693 반응식
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([OH:15])=O.[NH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[CH:23]=[O:24]>S(Cl)(Cl)=O.ClCCl.CCOC(C)=O>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([NH:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[CH:23]=[O:24])=[O:15]

참가 물질

6

반응물 2

HCID 27610334-AminonicotinaldehydeHCID 542654372,6-Dichloro-3-nitrophenylacetic acid

생성물 1

HCID 598338592-(2,6-dichloro-3-nitro-phenyl)-N-(3-formyl-pyridin-4-yl)-acetamide수율 95.2%

시약·촉매·용매 3

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매HCID 24386Thionyl Chloride용매

실험 절차

A solution of (2,6-dichloro-3-nitro-phenyl)-acetic acid (15.0 g, 60.0 mmol) in thionyl chloride (60 mL) is refluxed for one hour. The solvent is removed by concentration; dry toluene is added and concentrated to thoroughly remove thionyl chloride. To the solution of acid chloride in dry dichloromethane (200 mL) is added (drop-wise) a solution of 4-amino-pyridine-3-carbaldehyde (6.6 g, 54 mmol) in dichloromethane (50 mL) and DIEDA (10.7 mL, 60 mmol). The mixture is at room temperature for 2 hours. The reaction mixture is diluted with EtOAc (300 ml) and washed with saturated K2CO3 and brine. The organic layer is dried, filtered and concentrated to give crude product. Recrystallization with dichloromethane/hexane results in the titled compound as a solid (18.2 g, 95.2%).

후처리

  1. customThe solvent is removed by concentration
  2. additiondry toluene is added
  3. concentrationconcentrated to thoroughly remove thionyl chloride
  4. washwashed with saturated K2CO3 and brine
  5. customThe organic layer is dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give crude product
  9. customRecrystallization with dichloromethane/hexane

출처 및 근거

ORD 기록
ord-c0ea74fc44c74a67a44b70cbc2269a15
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449582B2

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