Hydrochloric Acid → HCID 57438892, compound

HRID 1669777Notes

Reaction equation

HRID 1669777 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]2[C:10]=1[C:11](=[O:21])[CH:12]=[C:13]([CH3:20])[O:14]2.[ClH:22]>C(#N)C.[Cu](Cl)Cl>[Cl:22][C:9]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]2[C:10]=1[C:11](=[O:21])[CH:12]=[C:13]([CH3:20])[O:14]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 57438891HCID 57438891, compound

Product 1

HCID 57438892HCID 57438892, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
65 °C

Procedure

0.42 g (3.9 mmol) of copper(II) chloride and 0.45 g (3.96 mmol) of tert-butyl nitrite are introduced into 20 ml of acetonitrile and heated to 65° C. 0.5 g (2.63 mmol) of 5-amino-2,8-dimethyl-4H-chromen-4-one in 10 ml of acetonitrile are slowly added dropwise to this suspension. The reaction mixture is stirred at 65° C. for 10 min and then allowed to cool to room temperature, and subsequently 5 ml of concentrated hydrochloric acid are added. After extraction with diethyl ether, the combined organic phases are washed with water and dried over sodium sulfate. After removal of the solvent in vacuo, the remaining crude product is purified by preparative HPLC. 0.27 g (50% of theory) of the title compound is obtained.

Workup

  1. temperatureto cool to room temperature
  2. extractionAfter extraction with diethyl ether
  3. washthe combined organic phases are washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent in vacuo
  6. customthe remaining crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-59bc7e224068417b8013c1eb517ded98
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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