Phosphorus oxychloride → HCID 86645343, compound

HRID 1949161Notes

Reaction equation

HRID 1949161 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](O)=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=2)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:24].C([O-])(O)=O.[Na+]>O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:24])=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178470052HCID 178470052, compound

Product 1

HCID 86645343HCID 86645343, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 150 mg (0.52 mmol) 7-tert-butyl-2-hydroxy-4-methyl-quinoline-3-carboxylic acid ethyl ester and POCl3 (1 ml) was heated for 2 h at 150° C. Then the reaction solution was poured into iced water (15 ml) and made alkaline with a saturated aqueous NaHCO3 solution. It was then extracted with EE and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. 140 mg (0.46 mmol, 88%) 7-tert-butyl-2-chloro-4-methyl-quinoline-3-carboxylic acid ethyl ester were obtained as the residue, which was reacted further with no additional purification.

Workup

  1. extractionIt was then extracted with EE
  2. washthe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-5b582cc1203048e9b2ee9ac05138152b
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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