Dimethyl Sulfate → Methyl 4-amino-5-chloro-2-hydroxybenzoate

HRID 5370

反応式

HRID 5370 の反応式
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:12])[CH:3]=1.C[O-].[Na+].CO.S(OC)(O[CH3:22])(=O)=O>CO.O>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([O:8][CH3:22])=[O:7])=[C:4]([OH:12])[CH:3]=1

参加物

6

反応物 3

HCID 6497Dimethyl SulfateHCID 148832224-Amino-5-chloro-2-hydroxybenzoic acidHCID 23694274Sodium methanolate methanol

生成物 1

HCID 14883223Methyl 4-amino-5-chloro-2-hydroxybenzoate収率 87%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of 4-amino-5-chloro-2-hydroxybenzoic acid (1.88 g, 10 mmol) in absolute methanol (20 mL) was treated with 25% sodium methoxide/methanol (2.16 g, 10 mmol), stirred for 30 minutes, and concentrated in vacuo. The solid residue was taken up in anhydrous acetone (30 mL), treated with dimethyl sulfate (1.64 g, 13 mmol), and refluxed for 2 hours. The resultant solution was diluted with water (100 mL), and the precipitate was filtered, washed with water, and dried exhaustively in vacuo to afford 1.75 g (87%) of fine colorless needles. The material was recrystallized from ethyl acetate/hexane; mp 138°-139° C.

後処理

  1. concentrationconcentrated in vacuo
  2. temperaturerefluxed for 2 hours
  3. filtrationthe precipitate was filtered
  4. washwashed with water
  5. customdried exhaustively in vacuo

出典と根拠

ORDレコード
ord-5ef4854df60141d78ca949d2c8047a2b
出典データセット
uspto-grants-1993_09
特許番号
US05244907

関連ノート

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