Ammonium Hydroxide → 4-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 253423Notes

Reaction equation

HRID 253423 reaction equation
[NH:1]1[C:5]2=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.O=P(Cl)(Cl)[Cl:13].[NH4+].[OH-]>>[Cl:13][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[C:4]=1[CH:3]=[CH:2][NH:1]2

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 178526243HCID 178526243, compound

Product 1

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Conditions

Temperature
125 °C

Procedure

4-chloro-7-azaindole 92 was synthesized by reacting 1H-Pyrrolo[2,3-b]pyridine 7-oxide 91 with a chlorinating agent (e.g. POCl3) neat as described by Schneller, S. W.; Luo, Jiann-Kuan. J. Org. Chem. 1980, 45:4045-4048. The resulting solution after heating for 3-5 h at elevated temperatures (100-150° C.) was neutralized with a base (e.g. NH4OH) until a solid precipitated. The solid was isolated by filtration.

Workup

  1. customprecipitated
  2. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-590178c599134b13ac225080831885d4
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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