Methyl4,6-dichloronicotinate → Methyl 6-chloro-4-methoxypyridine-3-carboxylate

HRID 251574ノート

反応式

HRID 251574 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9](Cl)=[CH:8][C:7]([Cl:11])=[N:6][CH:5]=1.[CH3:13][O-:14].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([O:14][CH3:13])=[CH:8][C:7]([Cl:11])=[N:6][CH:5]=1

参加物

4

反応物 2

HCID 2764083Methyl4,6-dichloronicotinateHCID 10942334Sodium Methoxide

生成物 1

HCID 22498691Methyl 6-chloro-4-methoxypyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 4,6-dichloro-nicotinic acid methyl ester (6.0 g, 29 mmol), NaOMe (2.0 g, 37 mmol) in THF (60 mL) is stirred overnight at room temperature. The solvent is removed in vacuo. Ice-cold dilute HCl solution is added to the solution. The mixture is neutralized with NaHCO3 and extracted with EtOAc. The extract is washed with water, dried, and concentrated. The residue is triturated with hexane until solid is formed. The solid is collected by filtration to give 6-chloro-4-methoxy-nicotinic acid methyl ester. 1H NMR (CDCl3) 8.72 (s, 1H), 6.91 (s, 1H), 3.97 (s, 3H), 3.90 (s, 3H).

後処理

  1. customThe solvent is removed in vacuo
  2. additionIce-cold dilute HCl solution is added to the solution
  3. extractionextracted with EtOAc
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is triturated with hexane until solid
  8. customis formed
  9. filtrationThe solid is collected by filtration

出典と根拠

ORDレコード
ord-23bf8aeeafff44c2854c66758f793103
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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