Phosphorus oxychloride → 4-Chloro-6-(2,6-diethyl-phenyl)-nicotinic acid methyl ester

HRID 251593ノート

反応式

HRID 251593 の反応式
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9](OC)=[CH:8][C:7]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:6][CH:5]=1.O=P(Cl)(Cl)[Cl:25]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([Cl:25])=[CH:8][C:7]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:6][CH:5]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 596780886-(2,6-Diethyl-phenyl)-4-methoxy-nicotinic acid methyl ester

生成物 1

HCID 596781594-Chloro-6-(2,6-diethyl-phenyl)-nicotinic acid methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6-(2,6-diethyl-phenyl)-4-methoxy-nicotinic acid methyl ester (4.0 g, 13.4 mmol), DMF (10 mL) and POCl3 (10 mL) is heated at 80° C. overnight. The volatile material is removed in vacuo. Ice water, NaHCO3 and hexane (50 mL) are added to the residue. The organic layer is separated and the aqueous layer is extracted with hexane (2×30 mL). The combined organic layer is washed with water, dried, and concentrated. The crude product is purified by silica gel chromatography (1% MeOH in CH2Cl2) to give 4-chloro-6-(2,6-diethyl-phenyl)-nicotinic acid methyl ester. 1H NMR (CDCl3) 9.12 (s, 1H), 7.40 (s, 1H), 7.30 (d, 1H), 7.15 (d, 2H), 4.00 (s, 3H), 2.30 (q, 4H), 1.05 (t, 6H).

後処理

  1. customThe volatile material is removed in vacuo
  2. additionIce water, NaHCO3 and hexane (50 mL) are added to the residue
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is extracted with hexane (2×30 mL)
  5. washThe combined organic layer is washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe crude product is purified by silica gel chromatography (1% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-361b770c922645ac9903c99da7066a29
出典データセット
uspto-grants-2011_01
特許番号
US07863454B2

反応ノート

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