Nitric Acid → HCID 67466494, compound

HRID 1046006Notes

Reaction equation

HRID 1046006 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[C:6]=1[I:12].[N+:18]([O-])([OH:20])=[O:19].C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:16]=[C:15]([N+:18]([O-:20])=[O:19])[C:14]([F:17])=[CH:13][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[C:6]=1[I:12]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 67466688HCID 67466688, compound

Product 1

HCID 67466494HCID 67466494, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A chilled (−10° C.) mixture of 4-(2,5-difluorophenoxy)-3-iodopyridin-2-amine (2.31 g, 6.64 mmol) in sulfuric acid (15 ml) was treated with nitric acid (0.35 ml, 7.96 mmol) while maintaining the temperature below 0° C. After stirring for 20 minutes, the mixture was poured into ice-cold 2 N aq. NaOH solution (100 mL of 2 N NaOH in ice) with stirring. The pH of the resultant solution was then made basic by careful addition or NaHCO3. After stirring for 30 min, the suspension was filtered, washed with water (3×10 mL) and dried to afford 4-(2,5-difluoro-4-nitrophenoxy)-3-iodopyridin-2-amine as light red solid (2.05 g, 79% yield). MS (ESI) m/z: 393.9 (M+H+).

Workup

  1. temperatureA chilled
  2. temperaturewhile maintaining the temperature below 0° C
  3. stirringwith stirring
  4. stirringAfter stirring for 30 min
  5. filtrationthe suspension was filtered
  6. washwashed with water (3×10 mL)
  7. customdried

Sources & evidence

ORD record
ord-9b6d9b5aeb504f0383e3f84d27ac17ee
Source dataset
uspto-grants-2013_10
Patent number
US08569319B2

Reaction notes

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