Sodium Carbonate → 3-Chloro-6-methoxyquinolin-4-ol

HRID 970388Notes

Reaction equation

HRID 970388 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.P(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.CN(C=O)C.O>[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

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 31398ChlorosuccinimideHCID 178487890HCID 178487890, compound

Product 1

HCID 1784878763-Chloro-6-methoxyquinolin-4-ol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Chloro-6-methoxy-quinolin-4-ol was prepared as described in WO 02\40474 by heating 6-methoxy-quinolin-4-ol with N-chloro-succinimide in acetic acid at 65° C. (96%) and (11 g) in dry DMF (80 mL) cooled in ice, was treated with phosphorus tribromide (15.6 g) and stirred at room temperature for 3.5 h. It was treated with iced-water, basified with sodium carbonate solution, and the solid collected and washed with water and dried in vacuo to afford a yellow solid (13.2 g).

Workup

  1. temperaturecooled in ice
  2. customthe solid collected
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b44ab9cf352e4e3bb013a77884db895d
Source dataset
uspto-grants-2007_12
Patent number
US07312212B2

Reaction notes

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