Nitric Acid → 7-Fluoro-1-(2-fluoro-ethyl)-5-nitro-1,3-dihydro-indol-2-one

HRID 2114886Notes

Reaction equation

HRID 2114886 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][F:13])[C:8](=[O:14])[CH2:7]2.[N+:15]([O-])([OH:17])=[O:16]>>[F:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][F:13])[C:8](=[O:14])[CH2:7]2

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 739475797-Fluoro-1-(2-fluoro-ethyl)-1,3-dihydro-indol-2-one

Product 1

HCID 739475807-Fluoro-1-(2-fluoro-ethyl)-5-nitro-1,3-dihydro-indol-2-one

Procedure

7-Fluoro-1-(2-fluoro-ethyl)-1,3-dihydro-indol-2-one (0.880 g, 0.0119 mol) is added portionwise to 70% nitric acid (8 ml) at −10° C. After the addition is complete, the reaction is allowed to warm to room temperature and then stirred for 24 hours. The mixture is diluted with ice water and the resulting precipitate filtered, washed with water, and dried under vacuum to give the title compound as a light brown solid. HPLC r.t. 4.65 min; MS for C10H8F2N2O3 m/z 243.3 (M+H)+.

Workup

  1. additionAfter the addition
  2. filtrationthe resulting precipitate filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8a5c39e54d3a42f1a067b722122fde5d
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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