Hydrochloric Acid → HCID 86729934, compound

HRID 61932Notes

Reaction equation

HRID 61932 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.O1CCCC1.[CH2:21]([Mg]Br)[CH:22]([CH3:24])[CH3:23].Cl>C/C(/[O-])=C\C(C)=O.C/C(/[O-])=C\C(C)=O.C/C(/[O-])=C\C(C)=O.[Fe+3].CN1CCCC1=O>[CH2:21]([C:2]1[C:11]2[C:6](=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1)[CH:22]([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 867299354-Chlorobenzo(h)quinazolineHCID 178418816HCID 178418816, compound

Product 1

HCID 86729934HCID 86729934, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 53384555HCID 53384555, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 100-mL three-neck flask were put 0.53 g (2.5 mmol) of 4-chlorobenzo[h]quinazoline, 52 mg (0.148 mmol) of tris(2,4-pentanedionato)iron(III) (abbreviation: Fe(acac)3), 25 mL of dehydrated tetrahydrofuran (THF), and 2.0 mL of 1-methyl-2-pyrrolidone (abbreviation: NMP), and the air in the flask was replaced with nitrogen. The flask was cooled with ice, 2.6 mL of isobutylmagnesium bromide solution (1 M in THF) (abbreviation: iBuMgBr) was added, and the mixture was stirred at room temperature for 16 hours. Then, 1 M hydrochloric acid was added, and an organic layer was subjected to extraction with ethyl acetate. The solution of the extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. After washing, anhydrous magnesium sulfate was added to the organic layer for drying. The resulting mixture was subjected to gravity filtration, and the filtrate was concentrated to give a residue. The residue was purified by silica gel column chromatography. As the developing solvent, first, dichloromethane was used; then, a 10:1 dichloromethane-ethyl acetate mixed solvent was used. The resulting fraction was concentrated to give 0.14 g of an orange oily substance in a yield of 24%. Synthesis Scheme (b-1) of Step 1 is shown below.

Workup

  1. customIn a 100-mL three-neck flask were put
  2. additionwas added
  3. extractionan organic layer was subjected to extraction with ethyl acetate
  4. washThe solution of the extract was washed with a saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  6. washAfter washing
  7. additionanhydrous magnesium sulfate was added to the organic layer
  8. customfor drying
  9. filtrationThe resulting mixture was subjected to gravity filtration
  10. concentrationthe filtrate was concentrated
  11. customto give a residue
  12. customThe residue was purified by silica gel column chromatography
  13. concentrationThe resulting fraction was concentrated
  14. customto give 0.14 g of an orange oily substance in a yield of 24%
  15. customSynthesis Scheme (b-1) of Step 1

Sources & evidence

ORD record
ord-684a38159f994bfc81ec091e1e73b4bd
Source dataset
uspto-grants-2016_09
Patent number
US09444059B2

Reaction notes

Loading…