Water → HCID 10247186, compound

HRID 1672345Notes

Reaction equation

HRID 1672345 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N+:8]([O-])=[CH:7][C:6]3[N:13]=[CH:14][N:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[Cl:22])[C:5]=3[C:4]=2[CH:3]=1.CN(C=O)C.O=P(Cl)(Cl)[Cl:30].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:30][C:7]1[C:6]2[N:13]=[CH:14][N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:5]=2[C:4]2[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:9]=2[N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 10359250HCID 10359250, compound

Product 1

HCID 10247186HCID 10247186, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 100 mg (0.30 mmol) of 8-chloro-1-(2-chloro-phenyl)-1H-imidazo[4,5-c]quinoline 5-oxide (Example 71), 50 μl dry DMF, and 86 μl POCl3 in 2 ml toluene is stirred at 70° C. bath temperature for 3½ h. First, ice is added to the cold reaction mixture, then water and ethyl acetate. The phases are separated and the water phase is extracted with ethyl acetate. The combined organic phases are washed with water and brine, then dried over Na2SO4. After the solvent is evaporated, the residue is crystallized from ethyl acetate-hexane. mp: 194-200° C.; MS: 348 (M++1); HPLC: tret=13.54 min (Grad 1).

Workup

  1. additionFirst, ice is added to the cold reaction mixture
  2. customThe phases are separated
  3. extractionthe water phase is extracted with ethyl acetate
  4. washThe combined organic phases are washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customAfter the solvent is evaporated
  7. customthe residue is crystallized from ethyl acetate-hexane
  8. customtret=13.54 min (Grad 1)

Sources & evidence

ORD record
ord-da54868e3e044bfd9960c58fa4c9d77a
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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