Water → 3-Azido-4-methylbenzoic acid

HRID 2099150Notes

Reaction equation

HRID 2099150 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1F)[C:7]([OH:9])=[O:8])([O-])=O.N([O-])=O.[Na+].[N-]=[N+:19]=[N-:20].[Na+].O.[C:23](O)(C(F)(F)F)=O>[Pd]>[N:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:23])[C:7]([OH:9])=[O:8])=[N+:19]=[N-:20]

Participants

7

Reactant 5

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 679874-Fluoro-3-nitrobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 179730913-Azido-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 1.04 g (5.62 mmol) 3-nitro-4-fluoro benzoic acid and 105 mg of Pd/C in 10 mL of TFA was stirred for 12 h under an H2 atmosphere. The mixture was then filtered through celite and the filter cake was washed with 20 mL of TFA. The pale yellow solution was then stirred under N2 at 0° C. for 10 min and 405 mg (5.87 mmol) of NaNO2 was added in small portions over 15 min. After an additional 15 min, 400 mg (6.15 mmol) of NaN3 was then added carefully in portions. Gas evolved slowly, and after 1 h the mixture was poured over 20 mL of water and 50 mL of ice. After the ice had melted, the resulting precipitate was filtered and washed with water and hexanes, then dried under vacuum to provide 964 mg of Compound 7 as a white powder.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washthe filter cake was washed with 20 mL of TFA
  3. stirringThe pale yellow solution was then stirred under N2 at 0° C. for 10 min
  4. waitAfter an additional 15 min
  5. filtrationthe resulting precipitate was filtered
  6. washwashed with water and hexanes
  7. customdried under vacuum

Sources & evidence

ORD record
ord-94e58ad8eb904daeac08571ef320fe12
Source dataset
uspto-grants-2009_08
Patent number
US07569568B2

Reaction notes

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