Pyridine-4-carbonyl chloride → HCID 10149810, 화합물

HRID 2182815노트

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HRID 2182815 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:4][CH:3]=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:11]([CH3:15])[CH:12]=[C:13]([C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[O:23])[CH:14]=2)=[O:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 417436Pyridine-4-carbonyl chlorideHCID 1116388(4-chlorophenyl)(1-methyl-1H-pyrrol-2-yl)methanoneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 10149810HCID 10149810, 화합물수율 27%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A solution of 17.5 g (0.08 mole) of (4-chlorophenyl)(1-methyl-1H-pyrrol-2-yl)methanone, 14.4 g (0.088 mole) of isonicotinoyl chloride and 26.6 g of aluminum chloride (0.2 mole) in 280 mL of DCE was heated under reflux for 16 h. After cooling, the mixture was partitioned between CH2Cl2 and dilute NaOH solution. The organic layer was dried and the solvent was evaporated in vacuo. The residue was triturated with ether. The resulting solid was recrystallized from 2-PrOH to give 7 g (27%) of the title compound, mp 174-175° C. ES-MS m/z=325 (M++H). 1H NMR (300 MHz, CDCl3) δ 4.1 (s, 3H); 7.1 (s, 1H); 7.3(dd, 2H); 7.42 (dd, 2H); 7.45 (s, 1H); 7.8 (dd, 2H); 8.8 (dd, 2H). Anal calc'd for: C18H13ClN2O2: C, 66.57; H, 4.03; N, 8.63. Found: C, 66.34; H, 3.94; N, 8.53.

후처리

  1. temperatureunder reflux for 16 h
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between CH2Cl2 and dilute NaOH solution
  4. customThe organic layer was dried
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was triturated with ether
  7. customThe resulting solid was recrystallized from 2-PrOH

출처 및 근거

ORD 기록
ord-5a3277f175fb41649eaadafccc6cb043
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06897319B2

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