Ammonia → 3-(1-Ethyl-2-methylindol-3-yl)-3-(1-methyl-2-naphthylindolizin-3-yl)phthalide

HRID 1680695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1680695
[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[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20](O)=[O:21])=[O:13])=[C:4]1[CH3:23])[CH3:2].C[C:25]1[C:26]([C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)C=2)=[CH:27][N:28]2[C:33]=1[CH:32]=[CH:31][CH:30]=[CH:29]2.C(O[C:48](=O)[CH3:49])(=O)C.N>C1(C)C=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([C:33]3[N:28]4[C:27]([CH:32]=[CH:31][CH:30]=[CH:29]4)=[C:26]([C:34]4[CH:43]=[CH:42][C:41]5[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:48]=4[CH3:49])[CH:25]=3)[C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:20](=[O:21])[O:13]2)=[C:4]1[CH3:23])[CH3:2]

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 3084978Benzoic acid, 2-[(1-ethyl-2-methyl-1H-indol-3-yl)carbonyl]-HCID 205369601-Methyl-2-(2-naphthyl) indolizine

Produkt 1

HCID 205369503-(1-Ethyl-2-methylindol-3-yl)-3-(1-methyl-2-naphthylindolizin-3-yl)phthalide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 3.0 grams of (1-ethyl-2-methylindol-3-yl) (2-carboxyphenyl)ketone, 2.5 grams of 1-methyl-2-(2-naphthyl) indolizine and 10 ml. of acetic anhydride was heated at 39° C. for about two hours. The resulting solution was cooled and added to a mixture of ice, toluene and ammonia. The toluene layer was separated, dried, treated with charcoal and filtered. Petroleum ether was added and after fractional precipitation a crystalline product was obtained and recrystallized from a toluene-heptane mixture to a constant melting point of 191°-193° C. A chloroform solution of this final product gave a blue color when applied to a record sheet material coated with a zinc-modified phenolic resin.

Aufarbeitung

  1. temperatureThe resulting solution was cooled
  2. customThe toluene layer was separated
  3. customdried
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. additionPetroleum ether was added
  7. customafter fractional precipitation a crystalline product
  8. customwas obtained
  9. customrecrystallized from a toluene-heptane mixture to a constant melting point of 191°-193° C

Quellen und Nachweise

ORD-Eintrag
ord-e7e470a3ad554fc4b140a17b75d1d87e
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04275206

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