Nitric Acid → N-(4-chloro-2-fluoro-5-nitrophenyl)acetamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O.OS(O)(=O)=O.O=S(=O)=O>[Cl:1][C:2]1[C:7]([N+:13]([O-:15])=[O:14])=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a stirred solution of 375.2 g (2 mole) of N-(4-chloro-2-fluorophenyl)acetamide in 600 mL of concentrated sulfuric acid and 400 mL of oleum (30%) was added 166 mL of a 1:1 mixture of nitric acid (100%) and concentrated sulfuric acid at 0° C. over a period of 1.5 hours. After the addition was complete, the reaction mixture was poured into 11 L of ice water. The precipitate was filtered and the filter cake suspended in 200 mL of water. The solid was redissolved by the addition of 2 L of ethyl acetate and neutralized with aqueous NaOH to pH 7. The two phase mixture was heated to 50° C. and separated. The organic layer was washed with 150 mL of water. 200 mL of ethyl acetate were distilled off and the remaining solution was treated with 12 g of Celite® at 70° C., filtered and washed with another 200 mL of ethyl acetate.
Workup
- additionAfter the addition
- filtrationThe precipitate was filtered
- dissolutionThe solid was redissolved by the addition of 2 L of ethyl acetate and neutralized with aqueous NaOH to pH 7
- customseparated
- washThe organic layer was washed with 150 mL of water
- distillation200 mL of ethyl acetate were distilled off
- additionthe remaining solution was treated with 12 g of Celite® at 70° C.
- filtrationfiltered
- washwashed with another 200 mL of ethyl acetate
Sources & evidence
- ORD record
- ord-082e78043443490fb49e6613931b3210
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06664400B2
Reaction notes
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