Acetyl chloride → 5-Chloroisatoic anhydride
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7](Cl)[C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13](OCC)=[O:14].C([Cl:21])(=O)C>O1CCOCC1>[Cl:21][C:8]1[CH:7]=[C:3]2[C:4]([O:6][C:13](=[O:14])[NH:1][C:2]2=[CH:10][CH:9]=1)=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2-Amino-6-chlorobenzoic acid (30 g) was suspended in 1,4-dioxane (225 ml) and ethyl chloroformate (75 ml) was added. The mixture was heated at reflux for 1 hour, then cooled to 50° C., and acetyl chloride (75 ml) was added. The mixture was stirred for 10 hours, after which the precipitated product was filtered off and washed with toluene. Drying in vacuum yields 5-chloroisatoic anhydride (33 g, 97% yield).
Workup
- temperatureThe mixture was heated
- temperatureat reflux for 1 hour
- filtrationafter which the precipitated product was filtered off
- washwashed with toluene
- customDrying in vacuum
Sources & evidence
- ORD record
- ord-95d444a5725d4f3d89bff7eb6a69388c
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560557B2
Reaction notes
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