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

HRID 2057636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2057636
[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-0f0a130eab5a49a2bd03ffc3866d7623
Quelldatensatz
uspto-grants-1980_07
Patentnummer
US04211872

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