Acetic Anhydride → 7(1-ethyl-2-methyl-3-indolyl)-7-(diphenylamino)furo[3,4-b]-pyridine-5(7H)-one

HRID 1388979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1388979
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:14]2[C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=2)=O)=[C:4]1[CH3:23])[CH3:2].C([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35]([C:37]2[C:38](C(O)=O)=NC=CC=2)=O)=[C:27]1[CH3:46])C.C1(NC2C=CC=CC=2)C=CC=CC=1.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2([N:26]([C:27]3[CH:28]=[CH:35][CH:37]=[CH:38][CH:46]=3)[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:19]3[C:20](=[O:22])[O:21]2)=[C:4]1[CH3:23])[CH3:2]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 11487DiphenylamineHCID 1090822-Pyridinecarboxylic acid, 3-[(1-ethyl-2-methyl-1H-indol-3-yl)carbonyl]-HCID 1123443-Pyridinecarboxylic acid, 2-((1-ethyl-2-methyl-1H-indol-3-yl)carbonyl)-

Produkt 1

HCID 205343067(1-ethyl-2-methyl-3-indolyl)-7-(diphenylamino)furo[3,4-b]-pyridine-5(7H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture containing 4.5 g. of an isomer mixture comprising 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-3-pyridinecarboxylic acid and 3-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-2-pyridinecarboxylic acid, 2.5 g. of diphenylamine and 30 ml. of acetic anhydride was stirred 6.5 hours, then treated with one ml. of pyridine and allowed to stand overnight. The reaction mixture was poured into 750 ml. of water and the resulting solid product was purified by column chromatography affording 7(1-ethyl-2-methyl-3-indolyl)-7-(diphenylamino)furo[3,4-b]-pyridine-5(7H)-one as a light orange solid, m.p. 132.5°-136° C. A toluene solution of the product contacted with acidic clay or phenolic resin developed an orange image.

Aufarbeitung

  1. additionA mixture containing 4.5 g
  2. additiontreated with one ml
  3. additionThe reaction mixture was poured into 750 ml
  4. customof water and the resulting solid product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-465f4d020f0949dba67b77abb2df175a
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04243250

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