Water → 5-fluoro-3,3-dimethyl-1-nitroso-2,3-dihydro-1H-indole

HRID 2381912Notes

Reaction equation

HRID 2381912 reaction equation
[N:1](OCCC(C)C)=[O:2].[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH2:14][C:13]2([CH3:20])[CH3:19].O>C(Cl)Cl>[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([N:1]=[O:2])[CH2:14][C:13]2([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 8053Isoamyl NitriteHCID 217125755-Fluoro-3,3-dimethylindoline

Product 1

HCID 866393625-fluoro-3,3-dimethyl-1-nitroso-2,3-dihydro-1H-indoleYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Isoamyl nitrite (3.4 mL, 25.42 mmol) is added to a solution of 5-fluoro-3,3-dimethyl-2,3-dihydro-1H-indole (3.75 g, 22.69 mmol) in DCM. The mixture is refluxed overnight. The mixture is cooled and portioned between DCM and water. The organic phase is separated, washed with saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo to afford 5-fluoro-3,3-dimethyl-1-nitroso-2,3-dihydro-1H-indole (4.23 g, 96%) as a solid. MS: 195 (M+H). 1H NMR (300 MHz, CD3Cl)): δ 7.77 (dd, 1H), 7.08-6.98 (m, 2H), 3.94 (s, 2H), 1.39 (s, 6H).

Workup

  1. temperatureThe mixture is refluxed overnight
  2. temperatureThe mixture is cooled
  3. customThe organic phase is separated
  4. washwashed with saturated aqueous NaHCO3, water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99ff25756e6b447bb37451b2d366265c
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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