Sodium Sulfite → 1-Acetyl-1,2-dihydro-3H-indol-3-one

HRID 1162166Notes

Reaction equation

HRID 1162166 reaction equation
S([O-])([O-])=O.[Na+].[Na+].[C:7]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([O:19]C(=O)C)=[CH:11]1)(=[O:9])[CH3:8]>O>[C:7]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[CH2:11]1)(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 24437Sodium SulfiteHCID 5836021-Acetyl-1H-indol-3-yl acetate

Product 1

HCID 5388191-Acetyl-1,2-dihydro-3H-indol-3-oneYield 73.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium sulfite (12.6 g, 0.1 mol) in water (180 mL) was heated to 70-75° C. under stirring, and the acetic acid 1-acetyl-1H-indol-3-yl ester of Example 1c (9.0 g, 0.041 mol) was added in small portions. The mixture was stirred at 70-75° C. for 1.5 h, and then kept at room temperature overnight. The solid product was filtered off, dried, dissolved in methylene chloride (40 mL) and flash-chromatographed on aluminum oxide with methylene chloride as an eluent to give 5.25 g (71%) of light yellow product; m.p. 138° C.

Workup

  1. stirringThe mixture was stirred at 70-75° C. for 1.5 h
  2. filtrationThe solid product was filtered off
  3. customdried
  4. dissolutiondissolved in methylene chloride (40 mL)
  5. customflash-chromatographed on aluminum oxide with methylene chloride as an eluent

Sources & evidence

ORD record
ord-c961e29b0db04da29bc5dcdc6f56f044
Source dataset
uspto-grants-2010_10
Patent number
US07820691B2

Reaction notes

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