P,P-Diphenylphosphinic azide → HCID 86645382, compound

HRID 222546Notes

Reaction equation

HRID 222546 reaction equation
C1(P([N:15]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[Cl:18][C:19]1[C:28](C(O)=O)=[CH:27][C:26]2[C:21](=[CH:22][C:23]([C:32]([F:35])([F:34])[F:33])=[CH:24][CH:25]=2)[N:20]=1.CCCCCC.CC(=O)OCC>C1C=CC=CC=1>[Cl:18][C:19]1[C:28]([NH2:15])=[CH:27][C:26]2[C:21](=[CH:22][C:23]([C:32]([F:35])([F:34])[F:33])=[CH:24][CH:25]=2)[N:20]=1

Participants

5

Reactant 3

HCID 199401P,P-Diphenylphosphinic azideHCID 13726377HCID 13726377, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 86645382HCID 86645382, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

20.6 g (75 mmol) of diphenyiphosphoryl azide were added at RT to a solution of 1.4 g (5 mmol) of 2-chloro-7-(trifluoromethyl)quinoline-3-carboxylic acid in benzene (500 ml), and the mixture was then heated for 5 h at 90° C. Concentration in vacuo was then carried out and the residue was taken up in THF (80 ml). 4N aq. LiOH soln. (30 ml) was added to this solution, and stirring was carried out for 1 h at RT. Dilution with water and extraction with EA were then carried out. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 9:1) of the residue yielded 310 mg (1.3 mmol, 26%) of 2-chloro-7-(trifluoromethyl)quinolin-3-amine.

Workup

  1. concentrationConcentration in vacuo
  2. addition(30 ml) was added to this solution
  3. extractionDilution with water and extraction with EA
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e06a80bbdced44b488041003945c4925
Source dataset
uspto-grants-2012_06
Patent number
US08207342B2

Reaction notes

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