Nitric Acid → 5-chloro-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

HRID 875645Notes

Reaction equation

HRID 875645 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[N+:12]([O-])([OH:14])=[O:13]>>[Cl:1][C:2]1[C:3]([F:11])=[C:4]2[C:10]([N+:12]([O-:14])=[O:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 534129535-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 602052745-chloro-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridineYield 86%

Procedure

5-Chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridine (1.2 g, 7.0 mmol) was added slowly to fuming nitric acid (10 mL) at 0° C. Upon completion of the addition, the reaction was stirred for 10 minutes, and then quenched with ice. Water was added until a precipitate formed, which was filtered, washed with water and dried to give the product 5-chloro-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (1.3 g, 86% yield).

Workup

  1. additionUpon completion of the addition
  2. customquenched with ice
  3. additionWater was added until a precipitate
  4. customformed
  5. filtrationwhich was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-f2c5c1708f5c463880228a393026ab5b
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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