Ceric ammonium nitrate → HCID 10309994, compound

HRID 857286Notes

Reaction equation

HRID 857286 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([O:20][S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2].[O:30]=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>O1CCOCC1.O.[NH4+].[Cl-]>[OH:30][C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([O:20][S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 10126776HCID 10126776, compound

Product 1

HCID 10309994HCID 10309994, compound

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
75 °C

Procedure

To solution of KBrO3 (1.1 eq) in 5 mL of dioxane/water (3/2; 0.14M) was added the quinoline of EXAMPLE 25 (1.0 eq) and CAN (0.1 eq). The mixture was stirred at 75° C. for 16 h, poured in saturated aqueous NH4Cl and extracted with CH2Cl2 (2×). The combined organic extracts were dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 1:1) afforded the title compound as a white solid.

Workup

  1. extractionextracted with CH2Cl2 (2×)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-381a7e53e46c419b99356283db5d229e
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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