1-Acetyl-5-fluoro-1H-indol-3-yl acetate → 1-Acetyl-5-fluoro-1,2-dihydro-3H-indol-3-one

HRID 2396824Notes

Reaction equation

HRID 2396824 reaction equation
C([O:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)[N:7]([C:15](=[O:17])[CH3:16])[CH:6]=1)(=O)C>S(=O)(=O)(O)O>[C:15]([N:7]1[C:8]2[C:13](=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5](=[O:4])[CH2:6]1)(=[O:17])[CH3:16]

Participants

3

Reactant 1

HCID 189863271-Acetyl-5-fluoro-1H-indol-3-yl acetate

Product 1

HCID 189863261-Acetyl-5-fluoro-1,2-dihydro-3H-indol-3-oneYield 88.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2.2 g of 3-acetoxy-1-acetyl-5-fluoroindole were added to 20 ml of 90% sulfuric acid and, after stirring for three quarters of an hour, the reaction mixture was diluted with 100 ml of ice-water. The precipitate was filtered off, washed with water and dried. There were obtained 1.6 g (83%) of 1-acetyl-5-fluoroindolin-3-one as beige crystals with a m.p. of 143°-144°.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-840aa906099b46bc8447a2d84a6a70d6
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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