Sodium Nitrate → 1-Ethyl-7-fluoro-5-nitro-1,3-dihydro-indol-2-one

HRID 2114879Notes

Reaction equation

HRID 2114879 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[CH2:5][C:4]1=[O:13])[CH3:2].[N+:14]([O-])([O-:16])=[O:15].[Na+]>FC(F)(F)C(O)=O>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[CH:9][C:10]=2[F:12])[CH2:5][C:4]1=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 692741661-Ethyl-7-fluoro-1,3-dihydro-indol-2-one

Product 1

HCID 692741011-Ethyl-7-fluoro-5-nitro-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-Ethyl-7-fluoro-1,3-dihydro-indol-2-one (3.45 g, 19.3 mmol) is added portionwise to a mixture of sodium nitrate (1.64 g, 19.3 mmol) and trifluoroacetic acid (60 ml) and stirred at room temperature for 5 hours. The reaction is diluted with ice water and the resulting precipitate filtered, washed with water, and dried under vacuum to give the title compound as a brownish-yellow solid. HPLC r.t. 4.88 min; MS for C10H9FN2O3 m/z 223.0 (M-H)−.

Workup

  1. filtrationthe resulting precipitate filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d92cf83147bf404cae8876a5967c311b
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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