Sodium hydride → HCID 178517456, compound

HRID 1728408Notes

Reaction equation

HRID 1728408 reaction equation
[C:1]([NH:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:19]([NH2:21])=[O:20])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>C(O)C>[OH:20][C:19]1[C:11]2[NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:21]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 152847253-Benzamidoindole-2-carboxamide

Product 1

HCID 178517456HCID 178517456, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-Benzamidoindole-2-carboxamide (276 mg), sodium hydride (5 mg) and ethanol (5 mL) was refluxed for 2 h. The reaction mixture was quenched with saturated ammonium carbonate and the product was extracted with methylene chloride. After drying over magnesium sulfate, the solvent was removed in vacuo and the residue was triturated with ether to afford 4-Hydroxy-2-phenyl-5H-indolo[3,2-d]pyrimidine (Compound 2) as a white solid.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe reaction mixture was quenched with saturated ammonium carbonate
  3. extractionthe product was extracted with methylene chloride
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-75d8b162af524a5bbe8db04cd38db1df
Source dataset
uspto-grants-1994_07
Patent number
US05326868

Reaction notes

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