Hydrochloric Acid → 6-fluoro-2-(hydroxyimino)-4-methyl-2,3-dihydro-1H-inden-1-one

HRID 717098Notes

Reaction equation

HRID 717098 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[C:4]([CH3:12])[CH:3]=1.Cl.[N:14](OCCC(C)C)=[O:15]>C(OCC)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[N:14][OH:15])[C:8]2=[O:11])=[C:4]([CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 111163836-Fluoro-4-methylindan-1-one

Product 1

HCID 1317341576-fluoro-2-(hydroxyimino)-4-methyl-2,3-dihydro-1H-inden-1-oneYield 75.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 6-fluoro-4-methyl-2,3-dihydro-1H-inden-1-one (1 g, 6.09 mmol) in a mixture of diethyl ether (10 mL) and concentrated HCl (10 mL) was added isopentyl nitrite (0.73 mL, 5.47 mmol) and stirred at RT for 3 h. The precipitated solid was collected by filtration and washed with MeOH to obtain 6-fluoro-2-(hydroxyimino)-4-methyl-2,3-dihydro-1H-inden-1-one as a brown solid (800 mg, 68%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with MeOH

Sources & evidence

ORD record
ord-e8d239efd18b41bdbe4bfe1dfd75fefe
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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