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

HRID 1952038Notes

Reaction equation

HRID 1952038 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

To 1H-Pyrrolo[2,3-b]pyridine (1, 16.0 g, 135 mmol) in water (110 mL), were added hexamethylenetetramine (26.0 g, 185 mmol), and acetic acid (55.0 mL, 967 mmol). The reaction was refluxed for 12 hours. Water (329 mL) was added and the reaction was cooled to room temperature. The reaction was filtrated and washed with water to give compound (46, 15.0 g, 76%). MS (ESI)[M+H+]+=147.

Workup

  1. temperatureThe reaction was refluxed for 12 hours
  2. filtrationThe reaction was filtrated
  3. washwashed with water
  4. customto give compound (46, 15.0 g, 76%)

Sources & evidence

ORD record
ord-7d31031979124cce8af00f19966c767b
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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