Water → HCID 67155782, compound

HRID 2196729Notes

Reaction equation

HRID 2196729 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH3:27])[CH2:5][C:6]1[N:17](S(C2C=CC=CC=2)(=O)=O)[C:9]2=[N:10][CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=[C:8]2[CH:7]=1.O.C(OCC)(=O)C>C1COCC1>[CH3:3][N:4]([CH3:27])[CH2:5][C:6]1[NH:17][C:9]2=[N:10][CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=[C:8]2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67155774HCID 67155774, compound

Product 1

HCID 67155782HCID 67155782, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Sodium hydroxide (1.11 mL, 1.11 mmol, 1M in water) was added to a solution of N,N-dimethyl-1-(5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)methanamine (0.10 g, 0.28 mmol) in THF (1.5 mL). The reaction mixture was heated at 70° C. for 16 hours. The reaction mixture was then cooled down and treated with water and ethyl acetate. The layers were then separated. The aqueous layer was extracted once with ethyl acetate. The organic layers were dried over sodium sulfate, filtered, and evaporated to afford N,N-dimethyl-1-(5-nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)methanamine (0.05 g, 82%).

Workup

  1. temperatureThe reaction mixture was then cooled down
  2. customThe layers were then separated
  3. extractionThe aqueous layer was extracted once with ethyl acetate
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-fd61735f992041f188ee4e0292f98593
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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