Acetic Acid → 5-chloro-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C1N2CN3CN(C2)CN1C3.[C:21](O)(=[O:23])C>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:21]=[O:23])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In a round bottom flask, 5-chloro-1H-pyrrolo[2,3-b]pyridine (1, 10.0 g, 65.5 mmol) was combined with hexamethylenetetramine (11.9 g, 85.2 mmol), acetic acid (28.3 mL, 0.498 mol) and 56.7 mL of water. The reaction was heated at reflux overnight, then 200 mL of water was added. After 30 minutes, solid material was collected by filtration and dried to give the desired compound (114, 7.0 g).
Workup
- temperatureThe reaction was heated
- temperatureat reflux overnight
- filtrationsolid material was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-f4d5c70bb0954c4ba840c615a87a0808
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096593B2
Reaction notes
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