Isoamyl Nitrite → 6-Fluoro-4-nitroso-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 2382116Notes

Reaction equation

HRID 2382116 reaction equation
[N:1](OCCC(C)C)=[O:2].[F:9][C:10]1[CH:11]=[CH:12][C:13]2[O:18][CH2:17][CH2:16][NH:15][C:14]=2[CH:19]=1>C(Cl)Cl>[F:9][C:10]1[CH:11]=[CH:12][C:13]2[O:18][CH2:17][CH2:16][N:15]([N:1]=[O:2])[C:14]=2[CH:19]=1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 162444596-Fluoro-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 866393826-Fluoro-4-nitroso-3,4-dihydro-2H-benzo[1,4]oxazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isoamyl nitrite is added to a solution of 6-fluoro-3,4-dihydro-2H-benzo[1,4]oxazine (1 g) in DCM (15 mL) and heated to reflux overnight. The reaction mixture is concentrated in vacuo and the residue is purified by silica gel chromatography eluting with 10% EtOAc in heptane to give 6-Fluoro-4-nitroso-3,4-dihydro-2H-benzo[1,4]oxazine (0.83 g).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customthe residue is purified by silica gel chromatography
  5. washeluting with 10% EtOAc in heptane

Sources & evidence

ORD record
ord-c614821056c248cf81d3702b9e6e3c91
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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