Nitric Acid → HCID 86654964, compound

HRID 712168Notes

Reaction equation

HRID 712168 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:3]=1.[N+:22]([O-])([OH:24])=[O:23]>OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:5]([NH:9][C:10](=[O:15])[C:11]([CH3:12])([CH3:13])[CH3:14])=[C:6]([N+:22]([O-:24])=[O:23])[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 66977376HCID 66977376, compound

Product 1

HCID 86654964HCID 86654964, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

To an ice-cold solution of N-(4-bromo-5-fluoro-2-(pyridin-2-yl)phenyl)pivalamide (17.5 g, 50.0 mmol) in conc. H2SO4 (50.0 mL) was added drop wise fuming HNO3 (10.0 mL). The resulting mixture was stirred at 0-10° C. for 1 h. After completion of reaction (by TLC), the mixture was poured onto 500 mL of crushed ice and stirred for 30 min followed by extraction with EtOAc (3×500 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude was triturated with Et2O to obtain the desired product as a yellow solid (15.0 g, 76%). MS: 396.23 [M+H]+.

Workup

  1. customAfter completion of reaction (by TLC)
  2. stirringstirred for 30 min
  3. extractionfollowed by extraction with EtOAc (3×500 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude was triturated with Et2O

Sources & evidence

ORD record
ord-82d99ebe6ae64fc79dd898b7c516db46
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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