Phosphorus oxychloride → HCID 23542034, compound

HRID 1793395Notes

Reaction equation

HRID 1793395 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:8][C:9]([C:11]1[C:20](=O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]=1[CH:22]1[CH2:24][CH2:23]1)=[O:10])[CH3:7].C(=O)(O)[O-].[Na+]>C(#N)C>[CH2:6]([O:8][C:9]([C:11]1[C:12]([CH:22]2[CH2:24][CH2:23]2)=[N:13][C:14]2[C:19]([C:20]=1[Cl:3])=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH3:7]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 23542035HCID 23542035, compound

Product 1

HCID 23542034HCID 23542034, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

Phosphorus oxychloride (0.77 ml, 0.082 mols) was added in one portion to a suspension of 2-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (1.0 g, 0.041 mols) in acetonitrile and the mixture was heated at 75° C. for 90 minutes (becomes a clear solution above 65° C.). The resulting light brown solution was poured into saturated sodium bicarbonate (100 ml); the suspension was extracted with ethyl acetate and the combined organic extracts were dried and concentrated in vacuo to leave 4-Chloro-2-cyclopropyl-quinoline-3-carboxylic acid ethyl ester (1.15 g, 106%) as an off-white solid. Rf (AcOEt)=0.73.

Workup

  1. customa clear solution above 65° C.
  2. extractionthe suspension was extracted with ethyl acetate
  3. customthe combined organic extracts were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4872319f5f1945ae911cbcc86e7b9e1a
Source dataset
uspto-grants-2006_07
Patent number
US07081456B2

Reaction notes

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