Phosphorus oxychloride → 2-Chloro-6-hydroxyquinoline-5-carbaldehyde

HRID 579450Notes

Reaction equation

HRID 579450 reaction equation
O=P(Cl)(Cl)[Cl:3].[OH:6][C:7]1[CH:16]=[CH:15][C:14]2[NH:13][C:12](=O)[CH:11]=[CH:10][C:9]=2[C:8]=1[CH:18]=[O:19]>CN(C=O)C>[Cl:3][C:12]1[CH:11]=[CH:10][C:9]2[C:8]([CH:18]=[O:19])=[C:7]([OH:6])[CH:16]=[CH:15][C:14]=2[N:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 866834296-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehyde

Product 1

HCID 866834282-Chloro-6-hydroxyquinoline-5-carbaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

POCl3 (973 μL, 10.4 mmol) was added dropwise to a DMF (5 mL) solution of 6-hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehyde (658 mg, 3.48 mmol) at 0° C. The mixture was stirred for 20 hours at 20° C. then cooled to 0° C. Upon addition of ice water the product precipitated. It was filtered, washed with water and dried on air to afford 580 mg (88%) of the title compound. MS (ESI): 208 (M+H)+. 1H NMR (δ, DMSO (2.5 ppm)): 11.95 (s, 1H, OH), 10.70 (s, 1H, CHO), 9.38, 8.10, 7.67 and 7.55 (4d, 4×1H).

Workup

  1. temperaturethen cooled to 0° C
  2. customprecipitated
  3. filtrationIt was filtered
  4. washwashed with water
  5. customdried on air

Sources & evidence

ORD record
ord-7faf204fdd1045f0a6c83dc6276b33e5
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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