HCID 17802073, compound → HCID 70362216, compound

HRID 1651489Notes

Reaction equation

HRID 1651489 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[C:16]([CH3:19])=[C:15]([CH3:20])[C:14]1=[O:21].[H][H]>C(OCC)(=O)C.[Pt]=O>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:11])[CH3:12])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[C@H:16]([CH3:19])[C@H:15]([CH3:20])[C:14]1=[O:21]

Participants

5

Reactant 2

HCID 17802073HCID 17802073, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70362216HCID 70362216, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9.4 g (0.03 mol) of N-(2-fluoro-4-chloro-5-isopropoxyphenyl)-2,3-dimethylmaleic acid imide and 500 mg of platinum oxide (PtO2) in 100 ml of ethyl acetate is hydrogenated with hydrogen at room temperature under normal pressure. After about 5 hours, when the absorption of hydrogen has ceased, the catalyst is filtered off and the filtrate is concentrated to dryness. 7.9 g (85% of the theoretical yield) of an almost colourless oil which is uniform in a thin-layer chromatogram are obtained as residue and crystallised from isopropyl ether. The cis-N-(2-fluoro-4-chloro-5-isopropoxyphenyl)-2,3-dimethyl-succinimide so obtained has a melting point of 101°-102°.

Workup

  1. customwhen the absorption of hydrogen
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated to dryness
  4. custom7.9 g (85% of the theoretical yield) of an almost colourless oil which
  5. customare obtained as residue
  6. customcrystallised from isopropyl ether

Sources & evidence

ORD record
ord-c0fa6602223a42e3af796b22be593255
Source dataset
uspto-grants-1990_05
Patent number
US04929272

Reaction notes

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