Hydrochloric Acid → 2-Oximino-1-indanone

HRID 2100709Notes

Reaction equation

HRID 2100709 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl.C([O:16][N:17]=O)CCC>CCOCC>[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[N:17][OH:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67351-IndanoneHCID 10996Butyl nitrite

Product 1

HCID 63990382-Oximino-1-indanoneYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1-indanone (19.5 g, 0.15 mol) in 200 ml of ether was added 15 ml of concentrated HCl, then a solution of n-butylnitrite (18.75 ml, 0.16 mol) in 50 ml of ether at room temperature. The resulting mixture was stirred for 2 h, the precipitate was collected and dried to yield a white solid (15.4 g, 65% yield). LC-MS: 162 (MH+)

Workup

  1. customat room temperature
  2. customthe precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-0319c309bed048e58fca0fb7dde24c35
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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