Ethanol → Ethyl 6-chloronicotinate

HRID 5985

反応式

HRID 5985 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH2:11](O)[CH3:12].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:11][CH3:12])=[O:7])=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 792226-Chloronicotinic acid

生成物 1

HCID 2799611Ethyl 6-chloronicotinate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 15.75 g (0.1 mol) 6-chloronicotinic acid, 6.9 g (0.15 mol) ethanol, 22.7 g (0.11 mol) dicyclohexylcarbodiimide and 3.7 g 0.03 mol) dimethylaminopyridine in 200 ml methylene chloride was heated at reflux for 2 hours. The mixture was allowed to cool, solvent removed in vacuo and residue subjected to flash chromatography to give the title compound as a low-melting white solid. PMR (CDCl3): δ1.44 (3 H, t, J~6.2 Hz) 4.44 (2 H, q, J~6.2 Hz), 7.44 (1 H, d, J~8.1 Hz), 8.27 (1 H, dd, J~8.1 Hz, 3 Hz), 9 02 (1 H, d, J3 Hz).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. customsolvent removed in vacuo and residue

出典と根拠

ORDレコード
ord-7d6fedb6c5194b37b83c946407de6f1b
出典データセット
uspto-grants-1993_09
特許番号
US05246962

関連ノート

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