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

HRID 888104Notes

Reaction equation

HRID 888104 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[C:21](O)=[O:22]>O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:21]=[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 962WaterSolvent

Procedure

A solution of 1H-Pyrrolo[2,3-b]pyridine (10 g, 84.7 mmol) and hexamethylenetetraamine (17.8 g, 127 mmol) was heated to reflux in a solution of 33% AcOH (100 mL) for 16 h. The mixture was diluted with water (100 mL), cooled in the refrigerator, and crystallized from the solution affording 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as white solid. MS (ES+): 147.1 (M+H). Calc'd. for C8H6N2O—146.05.

Workup

  1. temperaturecooled in the refrigerator
  2. customcrystallized from the solution

Sources & evidence

ORD record
ord-e7badd3c36ad4d4a814c8239454d493f
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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