N-(5-Chloro-2-hydroxy-3-nitrophenyl)acetamide → 2-Amino-4-chloro-6-nitrophenol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([OH:12])=[C:6]([NH:8]C(=O)C)[CH:7]=1>O.CC(O)C>[NH2:8][C:6]1[C:5]([OH:12])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=[C:2]([Cl:1])[CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 30 °C
Procedure
230.6 g (1 mole) of N-(5-chloro-2-hydroxy-3-nitrophenyl)acetamide prepared according to Example 1b was suspended in a mixture of 950 ml of water and 100 ml of 2-propanol under a mild nitrogen purge. 345 ml of 36% w/w hydrochloric acid was added followed by 25 ml of water. The mixture was heated to reflux in about 30° C., while vigorously stirring and refluxed for 2 hours. The mixture was cooled to 0-5° C. in about one hour and stirred for an additional hour at 0-5° C. The solid was filtered off, washed twice with 250 ml of water, and dried at 50° C. and 100 mbar under a gentle nitrogen stream till dry. Yield about 91%.
Workup
- custompurge
- addition345 ml of 36% w/w hydrochloric acid was added
- temperatureThe mixture was heated
- temperaturerefluxed for 2 hours
- temperatureThe mixture was cooled to 0-5° C. in about one hour
- stirringstirred for an additional hour at 0-5° C
- filtrationThe solid was filtered off
- washwashed twice with 250 ml of water
- customdried at 50° C.
- customtill dry
Sources & evidence
- ORD record
- ord-5d340187cde74400b9029df3ae5241e3
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423040B2
Reaction notes
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