Hydroxyamine hydrochloride → HCID 88876337, compound

HRID 2091601Notes

Reaction equation

HRID 2091601 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=O)[CH2:7][C:8]32[CH2:12][CH2:11]3)=[CH:4][CH:3]=1.Cl.[NH2:15][OH:16].CC([O-])=O.[Na+]>CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[N:15]/[OH:16])/[CH2:7][C:8]32[CH2:12][CH2:11]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 70654604Spiro[cyclopropane-1,1'-[1H]inden]-3'(2'H)-one, 6'-bromo-

Product 1

HCID 88876337HCID 88876337, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6′-bromospiro[cyclopropane-1,1′-inden]-3′(2′H)-one (2.1 g, 8.86 mmol), hydroxylamine HCl (1.23 g, 17.7 mmol) and NaOAc (4.32 g, 53.1 mmol) in MeOH (160 mL) was stirred overnight at room temperature. The reaction was concentrated, slurried water (40 mL), then sonicated and filtered. The precipitate was dried under high vacuum to give (E)-6′-bromospiro[cyclopropane-1,1′-inden]-3′(2′H)-one oxime (2.23 g, 100% yield) as a white solid. MS (EI) m/z=253.1[M+1]+.

Workup

  1. concentrationThe reaction was concentrated
  2. customslurried water (40 mL), then sonicated
  3. filtrationfiltered
  4. customThe precipitate was dried under high vacuum

Sources & evidence

ORD record
ord-4cd9500282894ee28f4bf548238bb1a9
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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