HCID 13519565, compound → HCID 13519557, compound

HRID 371137Notes

Reaction equation

HRID 371137 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH:17]4[CH2:18][CH2:19][CH:14]([CH:15]=[CH:16]4)[CH:13]2[C:12](=[O:20])[N:11]([CH3:21])[C:10]3=[O:22])[CH:5]=[CH:6][C:7]=1[Cl:8]>Cl.C(OCC)(=O)C.[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH:17]4[CH2:16][CH2:15][CH:14]([CH2:19][CH2:18]4)[CH:13]2[C:12](=[O:20])[N:11]([CH3:21])[C:10]3=[O:22])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 1

HCID 13519565HCID 13519565, compound

Product 1

HCID 13519557HCID 13519557, compoundYield 91.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8.0 g of the above dicarboximide, 0.8 g of platinum oxide and 3 drops of concentrated hydrochloric acid in 150 ml of ethyl acetate was hydrogenated in a Parr apparatus. The reaction mixture was filtered and the filtrate was concentrated in vacuo giving 7.4 g of 3a-(3,4-dichlorophenyl)hexahydro-2-methyl-4,7-ethano-1H-isoindole-1,3(2H)-dione as straw colored crystals, mp 126°-134° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bc7608f50fa848c4a7ee72cc8488dc4e
Source dataset
uspto-grants-1985_07
Patent number
US04529736

Reaction notes

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