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

HRID 1156204Notes

Reaction equation

HRID 1156204 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-55448f4f3bd24a449ff1622c8c344ca0
Source dataset
uspto-grants-1982_06
Patent number
US04334072

Reaction notes

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