Hydrochloric Acid → HCID 58574447, compound

HRID 1619350Notes

Reaction equation

HRID 1619350 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[N:7]3[CH2:20][CH2:19][C:14]4(OCC[O:15]4)[CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1.Cl>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[N:7]3[CH2:20][CH2:19][C:14](=[O:15])[CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58574404HCID 58574404, compound

Product 1

HCID 58574447HCID 58574447, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromo-9,10-dihydro-6H-spiro[azepino[2,1-b]quinazoline-8,2′-[1,3]dioxolan]-12(7H)-one (0.5 g, 1.43 mmol) and 4N HCl (4 mL) in THF (20 mL) was heated at reflux for 4 h. After it was cooled to rt, the reaction mixture was quenched with aq. Na2CO3 and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product.

Workup

  1. temperatureat reflux for 4 h
  2. customthe reaction mixture was quenched with aq. Na2CO3
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-19ab93fed6ad4c4783cf3b531e98ce61
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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