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

HRID 441307

반응식

HRID 441307 반응식
[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]

참가 물질

8

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 3582902,2-DiethoxytetrahydrofuranHCID 517045Sodium AcetateHCID 18984069HCID 18984069, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f416015af10e465481b4c8c9412673ac
출처 데이터셋
uspto-grants-1977_08
특허 번호
US04039543

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