Trifluoroacetic anhydride → HCID 67264449, compound

HRID 1687964Notes

Reaction equation

HRID 1687964 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][C:9](=[O:15])[NH:8][C:7]=2[CH:16]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[N+:30]([O-:33])([O-:32])=[O:31].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][C:9](=[O:15])[NH:8][C:7]=2[C:16]=1[N+:30]([O-:32])=[O:31].[CH3:1][O:2][C:3]1[C:4]([N+:30]([O-:33])=[O:31])=[CH:5][C:6]2[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][C:9](=[O:15])[NH:8][C:7]=2[CH:16]=1

Participants

6

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 24434Potassium NitrateHCID 66830652HCID 66830652, compound

Product 2

HCID 67263944HCID 67263944, compoundYield 22%HCID 67264449HCID 67264449, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-10 °C

Procedure

8-Methoxy-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (612 mg, 2.79 mmol) was dissolved in Acetonitrile (25 mL) and was cooled at −10° C. Trifluoroacetic anhydride (1.40 mL, 9.91 mmol) was added followed by Potassium nitrate (0.285 g, 2.82 mmol; Acros). After overnight stirring, the reaction was partitioned between aq. sodium hydroxide and DCM. The organic extract was chromatographed to afford two products, 8-Methoxy-5,5-dimethyl-9-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (310 mg, 42%) and 8-Methoxy-5,5-dimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (160 mg, 22%). 1H-NMR (CDCl3): 7.48 (m, 2H), 6.85 (d, 1H, J=8.8 Hz), 3.91 (s, 3H), 2.36 (t, 2H, J=7.2 Hz), 2.12 (t, 2H, J=7.2H), 1.42 (s, 6H).

Workup

  1. customthe reaction was partitioned between aq. sodium hydroxide and DCM
  2. extractionThe organic extract
  3. customwas chromatographed

Sources & evidence

ORD record
ord-5e3fe80ce1664b3d80b7e3973cce0716
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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