Hydrochloric Acid → 5,6-difluoro-2-hydroxyimino-3H-inden-1-one

HRID 2060882Notes

Reaction equation

HRID 2060882 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:12])[CH2:6][CH2:5]2.C([O:18][N:19]=O)CC(C)C.Cl.O>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:12])[C:6](=[N:19][OH:18])[CH2:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8053Isoamyl NitriteHCID 117689445,6-Difluoro-1-indanone

Product 1

HCID 766113455,6-difluoro-2-hydroxyimino-3H-inden-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5,6-difluoroindan-1-one (Preparation 76) (3.1 g, 18.4 mmol) in MeOH at 40° C. was added isoamylnitrite (3.22 mL, 23.9 mmol) followed by conc. HCl (1.8 mL). The reaction was stirred at 40° C. for 45 min, cooled to rt and poured into water (50 mL). The precipitate was collected by filtration and air-dried to give the title compound: δH(DMSO-d6) 3.77 (2H, s), 7.72-7.85 (2H, m), 12.79 (1H, s).

Workup

  1. temperaturecooled to rt
  2. filtrationThe precipitate was collected by filtration
  3. customair-dried

Sources & evidence

ORD record
ord-e8c56f54b8f349288f7fc305600142ef
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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