Trifluoroacetic acid → 7-Fluoro-1-methyl-5-nitro-1,3-dihydro-indol-2-one

HRID 2114867Notes

Reaction equation

HRID 2114867 reaction equation
FC(F)(F)C(O)=O.[N+:8]([O-:11])([O-])=[O:9].[Na+].[F:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[N:21]([CH3:23])[C:20](=[O:24])[CH2:19]2>>[F:13][C:14]1[CH:15]=[C:16]([N+:8]([O-:11])=[O:9])[CH:17]=[C:18]2[C:22]=1[N:21]([CH3:23])[C:20](=[O:24])[CH2:19]2

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24268Sodium NitrateHCID 119516747-Fluoro-1-methylindolin-2-one

Product 1

HCID 119516757-Fluoro-1-methyl-5-nitro-1,3-dihydro-indol-2-one

Procedure

To a stirring suspension of trifluoroacetic acid (15 mL) and sodium nitrate (0.381 g, 4.48 mmol) was added 7-fluoro-1-methyl-1,3-dihydro-indol-2-one (7, 0.740 g, 4.48 mmol) and the reaction stirred at room temp. After 3½ hrs material poured onto ice water, filtered off resulting a precipitate. Dried on buchner funnel under vacuum overnight to give the title compound. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 3.4 (d, J=2.7 Hz, 3H) 3.6 (s, 2H) 8.0 (m, 2H).

Workup

  1. additionAfter 3½ hrs material poured onto ice water
  2. filtrationfiltered off
  3. customresulting a precipitate
  4. customDried on buchner funnel under vacuum overnight

Sources & evidence

ORD record
ord-1d75cd2dbe4147a29321d04e1caf1470
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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