Nitric Acid → 7-Amino-5-fluoroindolin-2-one

HRID 1811192Notes

Reaction equation

HRID 1811192 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.S(=O)(=O)(O)O.[N+:17]([O-])(O)=O>>[NH2:17][C:9]1[CH:10]=[C:2]([F:1])[CH:3]=[C:4]2[C:8]=1[NH:7][C:6](=[O:11])[CH2:5]2

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 592500547-Amino-5-fluoroindolin-2-oneYield 62.5%

Procedure

5-Fluoro-1,3-dihydro-indol-2-one (5.0 g, 33 mmol) was added with 98% sulfuric acid (17.6 ml) and 65%-68% nitric acid (2.1 ml) in an ice-water bath with salt at −5° C. Upon the completion of the addition, the mixture was stirred for 1 hour at room temperature and added with ice-water until precipitate was formed. The solid was filtered and washed with water (50 ml×3) and recrystallized from acetic acid and water to give 7-amino-5-fluoro-1,3-dihydro-indol-2-one (4.0 g, 62.5%) as an orange solid.

Workup

  1. additionUpon the completion of the addition
  2. customwas formed
  3. filtrationThe solid was filtered
  4. washwashed with water (50 ml×3)
  5. customrecrystallized from acetic acid and water

Sources & evidence

ORD record
ord-c4fb75bf25df4711b8d29a759580ecec
Source dataset
uspto-grants-2013_01
Patent number
US08362251B2

Reaction notes

Loading…