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

HRID 1608779Notes

Reaction equation

HRID 1608779 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.C1N2CN3CN(C2)CN1C3.[C:20](O)(=[O:22])C>O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=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-carbaldehydeYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7-azaindole (23.6 g, 0.20 mol) and hexamethylenetetramine (42 g, 0.30 mol) in 33% acetic acid (84 g, 1.4 mol and 168 ml H2O) is refluxed for 6 h. The resulting clear yellow solution is diluted with water, and the product is allowed to crystallize in the refrigerator overnight. Recrystallization of the crude product from water gave almost pure title compound in 50% yield (14.9 g). m.p. 216°-218° C.

Workup

  1. customto crystallize in the refrigerator overnight
  2. customRecrystallization of the crude product from water

Sources & evidence

ORD record
ord-3aebdeb7779e4788832576ea69076970
Source dataset
uspto-grants-1995_03
Patent number
US05397787

Reaction notes

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