Sulfuric Acid → 4-Fluoro-7-methyl-1H-indole-2,3-dione

HRID 61272Notes

Reaction equation

HRID 61272 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]([NH:8][C:9](=[O:13])/[CH:10]=N\O)[CH:7]=1.[OH:15]S(O)(=O)=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]2[C:7]=1[C:10](=[O:15])[C:9](=[O:13])[NH:8]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 51922061(2Z)-N-(5-fluoro-2-methylphenyl)-2-hydroxyiminoacetamide

Product 1

HCID 167912144-Fluoro-7-methyl-1H-indole-2,3-dione

Conditions

Temperature
60 °C

Procedure

(Z)—N-(5-Fluoro-2-methylphenyl)-2-(hydroxyimino)acetamide (7.22, 37 mmol) was dissolved in neat H2SO4 (50 ml) and heated at 60° C. for 1 h. The resulting solid was collected by filtration and washed with water to yield the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.35 (bs, 1H), 7.45 (m, 1H), 6.73 (m, 1H), 2.25 (s, 3H).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-0384e3e14f4b4b8c9077aa96acf2e07d
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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