Acetic Anhydride → 7-(1-Ethyl-2-methylindol-3-yl)-7-(1,2-diphenylindolizin-3-yl)-5,7-dihydrofuro[3,4-b]pyridin-5-one

HRID 1680697Notes

Reaction equation

HRID 1680697 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[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:24]1([C:30]2[C:31]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:32][N:33]3[C:38]=2[CH:37]=[CH:36][CH:35]=[CH:34]3)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OC(=O)C)(=O)C>C(Cl)(Cl)Cl>[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:32]3[N:33]4[C:38]([CH:37]=[CH:36][CH:35]=[CH:34]4)=[C:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:31]=3[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:19]3[C:20](=[O:21])[O:22]2)=[C:4]1[CH3:23])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 1123443-Pyridinecarboxylic acid, 2-((1-ethyl-2-methyl-1H-indol-3-yl)carbonyl)-HCID 127473441,2-Diphenylindolizine

Product 1

HCID 205369547-(1-Ethyl-2-methylindol-3-yl)-7-(1,2-diphenylindolizin-3-yl)-5,7-dihydrofuro[3,4-b]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.6 grams of (1-ethyl-2-methylindol-3-yl) (3-carboxy-pyridin-2-yl)ketone, 1.85 grams of 1,2-diphenylindolizine and 10 ml. of acetic anhydride was heated at about 40° C. for 104 minutes and then cooled in an ice bath. The reaction mixture was filtered and the product was repeatedly recrystallized from a toluene-petroleum ether mixture until a constant melting point of 206.5°-207.5° C. was obtained. A chloroform solution of the final product produced a blue color when applied to a record sheet material coated with a zinc-modified phenolic resin.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe reaction mixture was filtered
  3. customthe product was repeatedly recrystallized from a toluene-petroleum ether mixture until a constant melting point of 206.5°-207.5° C.
  4. customwas obtained

Sources & evidence

ORD record
ord-f1e1e6d530a844fb91e1cf1f62e263cc
Source dataset
uspto-grants-1981_06
Patent number
US04275206

Reaction notes

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