Chlorosuccinimide → 3-Chloro-6-methoxyquinolin-4-ol

HRID 638979Notes

Reaction equation

HRID 638979 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[OH:13].[Cl:14]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:14][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[OH:13])=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178487890HCID 178487890, compound

Product 1

HCID 1784878763-Chloro-6-methoxyquinolin-4-olYield 96.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

6-Methoxy-quinolin-4-ol (18.5 g) in acetic acid (750 mL) was treated with N-chlorosuccinimide (15.52 g) and the mixture was heated at 60° C. for 4.5 hr, cooled, and evaporated. Excess sodium bicarbonate solution was added and the solid collected and washed with water and dried in vacuo at 40° C. overnight, to give a yellow solid (21.3 g).

Workup

  1. temperaturecooled
  2. customevaporated
  3. additionExcess sodium bicarbonate solution was added
  4. customthe solid collected
  5. washwashed with water
  6. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-8e249458ab124e0aa52d6dfbed5d2481
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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