Sodium Hydroxide → 5-Nitro-7-azaindole

HRID 563996Notes

Reaction equation

HRID 563996 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]#[C:12][Si](C)(C)C)[C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].[OH-].[Na+]>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[CH:11]=[CH:12][NH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 115287895-Nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine

Product 1

HCID 115211405-Nitro-7-azaindole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 500 mg 5-Nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine in 4 ml ethanol were added 93.5 mg sodium hydroxide, and the mixture was stirred under irradiation in a microwave-oven for 30 minutes (min) at 140° C. 20 equal batches of this kind were combined and evaporated. The residue was dissolved in 100 ml conc. hydrochloric acid and stirred for 30 min at RT. It was again evaporated and the residue was refluxed with THF for 30 min. Insoluble parts were removed by filtration, the filtrate was evaporated and the residue was chromatographed on silica in ethyl acetate/heptane mixtures.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in 100 ml conc. hydrochloric acid
  3. stirringstirred for 30 min at RT
  4. customIt was again evaporated
  5. temperaturethe residue was refluxed with THF for 30 min
  6. customInsoluble parts were removed by filtration
  7. customthe filtrate was evaporated
  8. customthe residue was chromatographed on silica in ethyl acetate/heptane mixtures

Sources & evidence

ORD record
ord-f5751c411a774b19aac44e85a64bb210
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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