Chlorine → HCID 131713832, compound
Reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.[Cl:17]Cl>C(O)(=O)C>[Cl:17][C:3]1[C:4]2[C:5](=[O:16])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH:14]=[CH:15][C:2]=1[OH:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
2-Hydroxyacridone (3.17 grams; 0.015 mole) and acetic acid were charged into a glass reaction vessel equipped with a stirrer and thermometer. The mixture was cooled to 15° C. and a solution of chlorine (0.015 mole) in acetic acid (2.5 ml) was added dropwise with stirring. After the addition was completed stirring was continued at room temperature overnight. After this time the reaction mixture was filtered to recover product. The product was then washed, dried and dissolved in tetrahydrofuran (50 ml). The solution was treated with triethylamine (2 ml). The treated solution was then filtered and the filtrate treated with activated charcoal. The filtrate was then stripped of solvent in a rotary evaporator to yield chloro-2-hydroxyacridone m.p. 184°-191° C.
Workup
- customequipped with a stirrer
- additionAfter the addition
- stirringwas completed stirring
- filtrationAfter this time the reaction mixture was filtered
- customto recover product
- washThe product was then washed
- customdried
- dissolutiondissolved in tetrahydrofuran (50 ml)
- additionThe solution was treated with triethylamine (2 ml)
- filtrationThe treated solution was then filtered
- additionthe filtrate treated with activated charcoal
- customThe filtrate was then stripped of solvent in a rotary evaporator
Sources & evidence
- ORD record
- ord-39e140ebc8be4e18800b4a4bf33c32c6
- Source dataset
- uspto-grants-1984_10
- Patent number
- US04474774
Reaction notes
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