Acetic Anhydride → 3-(1-Ethyl-2-methylindol-3-yl)-3-(1,2-diphenylindolizin-3-yl)phthalide

HRID 224518Notes

Reaction equation

HRID 224518 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]([OH:22])=O)=[O:13])=[C:4]1[CH3:23])[CH3:2].[C:24]1([C:30]2[CH:31]=[C:32]3[N:37]([C:38]=2C2C=CC=CC=2)[CH:36]=[CH:35][CH:34]=[CH:33]3)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O[C:49](=O)[CH3:50])(=O)C>>[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:38]3[N:37]4[C:32]([CH:33]=[CH:34][CH:35]=[CH:36]4)=[C:31]([C:50]4[CH:49]=[CH:6][CH:5]=[CH:4][CH:23]=4)[C:30]=3[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:20](=[O:22])[O:13]2)=[C:4]1[CH3:23])[CH3:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 89068Indolizine, 2,3-diphenyl-HCID 3084978Benzoic acid, 2-[(1-ethyl-2-methyl-1H-indol-3-yl)carbonyl]-

Product 1

HCID 205369683-(1-Ethyl-2-methylindol-3-yl)-3-(1,2-diphenylindolizin-3-yl)phthalide

Procedure

A mixture of 3.06 grams of (1-ethyl-2-methylindol-3-yl) (2-carboxyphenyl)ketone, 2.7 grams of 2,3-diphenylindolizine and 10 ml. of acetic anhydride was heated at about 50° C. for 107 minutes. The reaction mixture was cooled and filtered and the obtained product was recrystallized from a toluene-heptane mixture. The 3.3 grams of product were recrystallized from a toluene-heptane mixture to a constant melting point of 227°-227.5° C. A chloroform solution of the product when applied to silica gel produced a blue color.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customthe obtained product was recrystallized from a toluene-heptane mixture
  4. customThe 3.3 grams of product were recrystallized from a toluene-heptane mixture to a constant melting point of 227°-227.5° C
  5. customproduced a blue color

Sources & evidence

ORD record
ord-7d7c3d70c1d7498486b08d0b86a44e8c
Source dataset
uspto-grants-1980_11
Patent number
US04232887

Reaction notes

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