Isatin → HCID 178497562, compound

HRID 235253Notes

Reaction equation

HRID 235253 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH:13]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16](=O)[C:14]1=O>C(O)(=O)C>[CH:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]2[C:11]=1[N:12]=[C:16]1[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[N:13]=[C:14]1[NH:1]2.[C:3]1([C:4]([O:6][CH3:7])=[O:5])[C:2]2[N:1]=[C:16]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[N:13]=[C:14]3[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 7054IsatinHCID 5718252,3-Diaminobenzoic acid methyl ester

Product 2

HCID 178497562HCID 178497562, compoundHCID 178497588HCID 178497588, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 20 g of methyl 2,3-diaminobenzoate and 17.7 g of isatin in 230 ml of acetic acid was heated under reflux for an hour. After completion of the reaction, the reaction solution was allowed to stand at room temperature overnight, and the resulting precipitate was collected by filtration. The precipitate was purified by silica gel column chromatography to give methyl 4-indolo[2,3-b]quinoxalinecarboxylate and methyl 1-indolo[2,3-b]quinoxalinecarboxylate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for an hour
  3. customAfter completion of the reaction
  4. filtrationthe resulting precipitate was collected by filtration
  5. customThe precipitate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ecb2b9f3f34147949a52045ad035d058
Source dataset
uspto-grants-1997_01
Patent number
US05597921

Reaction notes

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