Pyridine-4-carbonyl chloride → HCID 10149810、化合物

HRID 2182815ノート

反応式

HRID 2182815 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 10149810HCID 10149810、化合物収率 27%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5a3277f175fb41649eaadafccc6cb043
出典データセット
uspto-grants-2005_05
特許番号
US06897319B2

反応ノート

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