Acetic Acid → 5-chloro-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde

HRID 509966Notes

Reaction equation

HRID 509966 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]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 468564775-chloro-1H-pyrrolo(2,3-b)pyridine-3-carbaldehydeYield 59.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. filtrationsolid material was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-f4d5c70bb0954c4ba840c615a87a0808
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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