Ammonia → 2-Chloroquinolin-6-ol

HRID 1869793Notes

Reaction equation

HRID 1869793 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.N.O=P(Cl)(Cl)[Cl:17]>CN(C=O)C>[Cl:17][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

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178515777HCID 178515777, compound

Product 1

HCID 221325772-Chloroquinolin-6-olYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

A solution of 2,6-quinolinediol 10 (5 g) in POCl3 (21 ml) and DMF (3.4 ml) is stirred for 12 h at room temperature, then heated for 1 h at 115° C. The reaction is poured into water (100 ml) at 0° C. and neutralized with a 32% aqueous NH3 solution. The solid obtained by filtration is washed with acetone, and the resulting organic phase is evaporated to give 2-chloro-6-quinolinol 11 as a solid. No further purification is needed.

Workup

  1. customThe solid obtained by filtration
  2. washis washed with acetone
  3. customthe resulting organic phase is evaporated

Sources & evidence

ORD record
ord-ab0d49cc32a54b02b31f4fd44732f05e
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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