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

HRID 1413738

Reaktionsgleichung

Reaktionsgleichung von HRID 1413738
[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]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-333c51cacd6c4edead52ae2526715334
Quelldatensatz
uspto-grants-1981_02
Patentnummer
US04251454

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