Potassium Hydroxide → 4-Methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

HRID 398341Notes

Reaction equation

HRID 398341 reaction equation
[OH-].[K+].C([N:6]1[C:14]2[C:9](=[C:10]([CH3:15])[CH:11]=[CH:12][N:13]=2)[CH2:8][CH2:7]1)(=O)C>CO>[CH3:15][C:10]1[CH:11]=[CH:12][N:13]=[C:14]2[C:9]=1[CH2:8][CH2:7][NH:6]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23000253HCID 23000253, compound

Product 1

HCID 123987384-Methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

Potassium hydroxide (1 M, 5 mL) was added to a stirred solution of N-acetyl-4-methyl-7-azaindoline (0.78 g, 4.75 mmol) in methanol (10 mL) and the resulting mixture was heated to 55° C. for 4 h. The mixture was cooled and partitioned between methylene chloride and dilute ammonium hydroxide solution. The organic layer was dried (Na2SO4) and evaporated in vacuo to give the title compound as a yellow solid:

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between methylene chloride and dilute ammonium hydroxide solution
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-1f9dde4644eb4a3898903e086b7d9995
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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