Sodium → 4-Chloro-6-fluoro-2-methoxy-3-nitrophenylamine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9]C(=O)C)=[C:4]([O:13][CH3:14])[C:3]=1[N+:15]([O-:17])=[O:16].[Na]>Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH2:9])=[C:4]([O:13][CH3:14])[C:3]=1[N+:15]([O-:17])=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A suspension of 40.0 g (152 mmol) of N-(4-chloro-6-fluoro-2-methoxy-3-nitrophenyl)acetamide in 800 ml of 6M hydrochloric acid was heated for 5 hours at reflux temperature, whereupon the mixture was stirred overnight at approximately 20° C. For work-up, the reaction mixture was stirred into ice-water. The pH was brought to 8-9 by adding sodium solution. The mixture was subsequently extracted six times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and then concentrated under reduced pressure. Yield: 33 g (98%);
Workup
- temperaturewas heated for 5 hours
- temperatureat reflux temperature
- extractionThe mixture was subsequently extracted six times with ethyl acetate
- dry with materialThe combined organic phases were dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-035b001e45484f1e8bfe8129ab85ad10
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06602825B1
Reaction notes
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