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

HRID 270693

反応式

HRID 270693 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 24386Thionyl Chloride溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c0ea74fc44c74a67a44b70cbc2269a15
出典データセット
uspto-grants-2008_11
特許番号
US07449582B2

関連ノート

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