Hydrochloric Acid → 2-Chloroquinolin-6-ol

HRID 639360Notes

Reaction equation

HRID 639360 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1O.O=P(Cl)(Cl)[Cl:15].C(=O)(O)[O-].[Na+].Cl>C1COCC1.C(OCC)(=O)C.CN(C=O)C>[Cl:15][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=2)[N:1]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178515777HCID 178515777, compound

Product 1

HCID 221325772-Chloroquinolin-6-ol

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of quinoline2,6-diol (1 eq) in THF (0.25 M) was treated with POCl3 (1.1 eq) and a drop of DMF. Crushed ice was added to the reaction mixture and EtOAc was added and neutralized with a solution of sodium bicarbonate. The mixture was brought back to pH 6-7 with 1N HCl and ethyl acetate layer was separated, washed with water and brine to provide title compound.

Workup

  1. additionwas added
  2. customwas separated
  3. washwashed with water and brine

Sources & evidence

ORD record
ord-f9d6ceb77f4f4d379010dcbd24336685
Source dataset
uspto-grants-2010_04
Patent number
US07691866B2

Reaction notes

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