Sodium Bicarbonate → HCID 67155820, compound

HRID 2196730Notes

Reaction equation

HRID 2196730 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][C:4]1[NH:15][C:7]2=[N:8][CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=[C:6]2[CH:5]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CO>[CH3:16][N:2]([CH2:3][C:4]1[NH:15][C:7]2=[N:8][CH:9]=[C:10]([NH2:12])[CH:11]=[C:6]2[CH:5]=1)[CH3:1]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 67155782HCID 67155782, compound

Product 1

HCID 67155820HCID 67155820, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

SnCl2 dihydrate (0.11 g, 0.463 mmol) was added to a solution of N,N-dimethyl-1-(5-nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)methanamine (0.017 g, 0.077 mmol) in ethyl acetate (0.8 mL) and methanol (0.2 mL). The mixture was heated at 75° C. for 2 hours, after which saturated aqueous sodium bicarbonate was added. The salts were filtered off, and then the layers were separated. The organic layers were dried over sodium sulfate, filtered, and evaporated to afford 2-((dimethylamino)methyl)-1H-pyrrolo[2,3-b]pyridin-5-amine (0.008 g, 50%).

Workup

  1. filtrationThe salts were filtered off
  2. customthe layers were separated
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-8619b6e28a184aabb1e06af037036ea1
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

Loading…