HCID 11674039, compound → HCID 23585453, compound

HRID 2407062Notes

Reaction equation

HRID 2407062 reaction equation
N[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[N:7]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[C:8]([CH:12]([CH3:14])[CH3:13])=[N:9]2)=[CH:4][CH:3]=1.N([O-])=[O:24].[Na+]>S(=O)(=O)(O)O.O.O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([N:7]2[C:6](=[O:22])[C:5]3[C:10](=[CH:11][C:2]([OH:24])=[CH:3][CH:4]=3)[N:9]=[C:8]2[CH:12]([CH3:14])[CH3:13])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 11674039HCID 11674039, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23585453HCID 23585453, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21910475Sulfuric acid hydrate (1:1)Solvent2×

Conditions

Temperature
2.5 °C

Procedure

To a suspension of the compound of Example 1 (778 mg, 2.479 mmol) in concentrated sulphuric acid/water 972 μL/1.4 mL, cooled to ice bath temperature, is added a solution of sodium nitrite (188 mg) in water (680 μL). The mixture is stirred for 45 minutes at 0-5° C. (internal temperature) and then added to sulphuric acid/water 3/2 (5 mL), pre-heated to 150° C. After stirring for 15 minutes, the mixture is allowed to cool to room temperature, filtered and extracted with EtOAc (3×). The combined EtOAc extracts are washed with water, dried (Na2SO4) and evaporated to a yellow-orange solid. Purification by automated flash chromatography (gradient elution: EtOAc/hexane 0-25%) provides the title compound as a yellow solid.

Workup

  1. temperaturecooled to ice bath temperature
  2. temperaturepre-heated to 150° C
  3. stirringAfter stirring for 15 minutes
  4. temperatureto cool to room temperature
  5. filtrationfiltered
  6. extractionextracted with EtOAc (3×)
  7. washThe combined EtOAc extracts are washed with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated to a yellow-orange solid
  10. customPurification
  11. washby automated flash chromatography (gradient elution: EtOAc/hexane 0-25%)

Sources & evidence

ORD record
ord-8c846a06334e45a6a34f6d639f1a263c
Source dataset
uspto-grants-2014_08
Patent number
US08809528B2

Reaction notes

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