Benzoyl chloride, 2-chloro-5-nitro- → 2-Chloro-5-nitro-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)-benzamide

HRID 563998Notes

Reaction equation

HRID 563998 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[Cl:11][C:12]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:13]=1[C:14](Cl)=[O:15]>N1C=CC=CC=1.ClCCl>[Cl:11][C:12]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:13]=1[C:14]([NH:10][C:8]1[CH:9]=[C:4]2[CH:3]=[CH:2][NH:1][C:5]2=[N:6][CH:7]=1)=[O:15]

Participants

5

Reactant 2

HCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 117151871H-pyrrolo(2,3-b)pyridin-5-amine

Product 1

HCID 670082132-Chloro-5-nitro-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)-benzamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

1.87 g 1H-Pyrrolo[2,3-b]pyridin-5-ylamine in 60 ml dry pyridine were treated dropwise at RT with a solution of 6.79 g 2-chloro-5-nitrobenzoyl chloride in 10 ml dichloromethane. Stirring was continued over night. The mixture was evaporated and the residue was treated with 25 ml methanol and 10 ml conc. ammonia for 2 hrs at RT. The solvents are again evaporated and the residue is dispersed in water. The crude product is isolated by filtration and washed thoroughly with water and diethylether.

Workup

  1. waitwas continued over night
  2. customThe mixture was evaporated
  3. additionthe residue was treated with 25 ml methanol and 10 ml conc. ammonia for 2 hrs at RT
  4. customThe solvents are again evaporated
  5. additionthe residue is dispersed in water

Sources & evidence

ORD record
ord-b130c912c1e941c7a65caef297bdae47
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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