Chlorine → HCID 20456887, compound

HRID 1262556Notes

Reaction equation

HRID 1262556 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[Cl:16]Cl>C(O)(=O)C>[Cl:16][C:3]1[C:4]2[C:13](=[N:12][C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:14]=[CH:15][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 315322-Acridinol

Product 1

HCID 20456887HCID 20456887, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
15 °C

Procedure

2-Hydroxyacridine (3.17 grams; 0.015 mole) and acetic acid (100 ml) are charged into a glass reaction vessel equipped with a stirrer and thermometer. The mixture is cooled to 15° C. and a solution of chlorine (0.015 mole) in acetic acid (25 ml) is added dropwise with stirring. After the addition is completed stirring is continued at room temperature overnight. After this time the reaction mixture is filtered to recover product. The product is then washed, dried and dissolved in tetrahydrofuran (50 ml). The solution is treated with triethylamine (2 ml). The treated solution is then filtered and the filtrate treated with activated charcoal. The filtrate is then stripped of solvent in a rotary evaporator to yield chloro-2-hydroxyacridine.

Workup

  1. customequipped with a stirrer
  2. additionAfter the addition
  3. stirringis completed stirring
  4. filtrationAfter this time the reaction mixture is filtered
  5. customto recover product
  6. washThe product is then washed
  7. customdried
  8. dissolutiondissolved in tetrahydrofuran (50 ml)
  9. additionThe solution is treated with triethylamine (2 ml)
  10. filtrationThe treated solution is then filtered
  11. additionthe filtrate treated with activated charcoal
  12. customThe filtrate is then stripped of solvent in a rotary evaporator

Sources & evidence

ORD record
ord-e2158c6aa7a24c4d9148cd0096a6e4d8
Source dataset
uspto-grants-1984_06
Patent number
US04452792

Reaction notes

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