Acetic Acid → 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

HRID 641892Notes

Reaction equation

HRID 641892 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C1N2CN3CN(C2)CN1C3.[C:20](O)(=[O:22])C>O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:20]=[O:22])=[CH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 92221H-Pyrrolo(2,3-b)pyridine

Product 1

HCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into a 250 mL round bottom flask was placed 1H-pyrrolo[2,3-b]pyridine (10 g, 84.75 mmol). To this was added HMTA (hexamethylenetetramine) (17.8 g, 126.99 mmol). Addition of acetic acid (36 mL) was next. To the mixture was added H2O (70 mL). The resulting solution was allowed to react, with stirring, for 4 hours while the temperature was maintained at reflux in a bath of oil. The resulting solution was diluted with 200 mL of H2O. The reaction mixture was cooled. A filtration was performed and the filtrate cake was washed with H2O. This resulted in 7.5 g (61%) of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as a white solid.

Workup

  1. customInto a 250 mL round bottom flask was placed
  2. customto react
  3. temperaturewas maintained
  4. temperatureat reflux in a bath of oil
  5. temperatureThe reaction mixture was cooled
  6. filtrationA filtration
  7. washthe filtrate cake was washed with H2O
  8. customThis resulted in 7.5 g (61%) of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as a white solid

Sources & evidence

ORD record
ord-28f26eb11c3041d0ad608693b166db0a
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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