Isoamyl Nitrite → HCID 6813148, compound

HRID 1045651Notes

Reaction equation

HRID 1045651 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[N:18](OCCC(C)C)=[O:19]>C(OCC)C.C(O)(C)(C)C>[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[N:18][OH:19]

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 107241-TetraloneHCID 23665647Potassium tert-butoxide

Product 1

HCID 6813148HCID 6813148, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent

Procedure

Tetralone (25 g, 171 mmol) was added to a solution of potassium tert-butoxide (22 g, 196 mol) and isoamyl nitrite (26 g, 222 mmol) in diethyl ether (200 ml) and tert-butanol (200 ml). The solution was stirred at room temperature for 4 hours and then filtered to collect the potassium salt of the oxime. The solid was dissolved with 1 N aqueous hydrochloric acid (200 ml) and extracted with chloroform and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was washed with ethyl acetate, and dried to give 3,4-dihydro-[1,2]naphthoquinone 2-oxime (21.5 g, 123 mmol, 72%) as brown crystals.

Workup

  1. filtrationfiltered
  2. customto collect the potassium salt of the oxime
  3. dissolutionThe solid was dissolved with 1 N aqueous hydrochloric acid (200 ml)
  4. extractionextracted with chloroform
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of the solvent
  7. washthe residue was washed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-5abc01ed79b943adb6a617df91ef1391
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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