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

HRID 1157023Notes

Reaction equation

HRID 1157023 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](O)=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=2)=O)=[C:4]1[CH3:23])[CH3:2].C(N1C2C(=CC=CC=2)C(C(C2C(C(O)=O)=NC=CC=2)=O)=C1C)C.[C:47]1([NH:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=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:53]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:19]3[CH2:20][O:21]2)=[C:4]1[CH3:23])[CH3:2]

Participants

6

Reactant 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)-

Product 1

HCID 867384577-(1-Ethyl-2-methyl-3-indolyl)-7-(diphenylamino)furo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e9debdda7acf4322b4aeeafe044f0bf7
Source dataset
uspto-grants-1982_06
Patent number
US04337340

Reaction notes

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