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

HRID 1923914Notes

Reaction equation

HRID 1923914 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:13])=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)[CH3:2].[N+:14]([O-])([OH:16])=[O:15]>>[CH2:1]([O:3][C:4]1[C:5]([F:13])=[C:6]2[C:12]([N+:14]([O-:16])=[O:15])=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)[CH3:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 60205637HCID 60205637, compound

Product 1

HCID 602056385-ethoxy-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridineYield 78%

Conditions

Temperature
0 °C

Procedure

Cold (about 0 to about 5° C.) fuming nitric acid (10 mL) was added to 5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridine (340 mg, 0.944 mmol). The reaction was stirred at 0° C. for 15 minutes and then ice was added. The resulting solid was filtered and dried to yield 5-ethoxy-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (165 mg, 78% yield) as a solid.

Workup

  1. additionice was added
  2. filtrationThe resulting solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-abb4265ebd354554b0d48f6a54b0c63d
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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