Hydroxyamine hydrochloride → 1-(2,6-dichloro-3-methylphenyl)-3-hydroxyiminoindol-2-one

HRID 465977Notes

Reaction equation

HRID 465977 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=O)[C:11]1=[O:20].Cl.[NH2:22][OH:23]>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[N:22][OH:23])[C:11]1=[O:20]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 19815161HCID 19815161, compound

Product 1

HCID 1784253951-(2,6-dichloro-3-methylphenyl)-3-hydroxyiminoindol-2-oneYield 81.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(2,6-dichloro-3-methylphenyl)-1H-indole-2,3-dione (0.3 g) and hydroxylamine hydrochloride (0.07 g) in pyridine (2 ml) is stirred at room temperature for 20 minutes. The reaction mixture is diluted with ethyl acetate (20 ml) and washed with 1 N HCl (2×100 ml). The organic layer is dried (MgSO4) and evaporated. Flash chromatography (silica, CH2Cl2) followed by recrystallization from isopropyl ether affords 1-(2,6-dichloro-3-methylphenyl)-1H-indole-2,3-dione 3-oxime (256 mg, 80%), mp 190°-191° C.

Workup

  1. washwashed with 1 N HCl (2×100 ml)
  2. dry with materialThe organic layer is dried (MgSO4)
  3. customevaporated
  4. customFlash chromatography (silica, CH2Cl2) followed by recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-1785f8001c7a424fb5b1c4a407829b50
Source dataset
uspto-grants-1992_10
Patent number
US05155110

Reaction notes

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