p-Toluenesulfonic acid → Methyl 3-amino-4-methyl-5-(1H-pyrrol-1-yl)benzoate

HRID 441307

反応式

HRID 441307 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([NH2:13])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[C:14]1(C)[CH:19]=CC(S(O)(=O)=O)=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+].C(OC1(OCC)CCCO1)C>O.C(O)C.C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:13]2[CH:16]=[CH:15][CH:14]=[CH:19]2)[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]

参加物

8

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 3582902,2-DiethoxytetrahydrofuranHCID 517045Sodium AcetateHCID 18984069HCID 18984069、化合物

生成物 1

HCID 20290401Methyl 3-amino-4-methyl-5-(1H-pyrrol-1-yl)benzoate

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of 18 g. of methyl 3,5-diamino-4-methylbenzoate, 0.7 g. of p-toluenesulfonic acid, 8.2 g. of sodium acetate, 32 g. of diethoxytetrahydrofuran, 10 ml of glacial acetic acid, 100 ml. of ethanol and 100 ml. of water was boiled at reflux for 3 hours. The alcohol was removed in vacuo and the residue extracted with ethyl acetate. The ethyl acetate solution was washed with water, dried over sodium sulfate and evaporated. By purification of the residue over aluminum oxide with ethyl acetate and recrystallization from high-boiling petroleum ether, there was obtained methyl 3-amino-4-methyl-5-(pyrrol-1-yl)benzoate, having a melting point of 112° C.

後処理

  1. additionA mixture of 18 g
  2. temperatureat reflux for 3 hours
  3. customThe alcohol was removed in vacuo
  4. extractionthe residue extracted with ethyl acetate
  5. washThe ethyl acetate solution was washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customBy purification of the residue over aluminum oxide
  9. customwith ethyl acetate and recrystallization from high-boiling petroleum ether

出典と根拠

ORDレコード
ord-f416015af10e465481b4c8c9412673ac
出典データセット
uspto-grants-1977_08
特許番号
US04039543

関連ノート

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