Methanol → N-(3-Amino-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1903894Notes

Reaction equation

HRID 1903894 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:15](=[O:16])[C:14]3[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[C:12]2=[O:21])[CH:7]=[CH:8][C:9]=1[Cl:10])([O-])=O.CO>O=[Pt]=O.CCOC(C)=O>[NH2:1][C:4]1[CH:5]=[C:6]([N:11]2[C:15](=[O:16])[C:14]3[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[C:12]2=[O:21])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 2

HCID 887MethanolHCID 1568791H-Isoindole-1,3(2H)-dione, 2-(4-chloro-3-nitrophenyl)-4,5,6,7-tetrahydro-

Product 1

HCID 13285967N-(3-Amino-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimideYield 80.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 40 g of N-(3-nitro-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide in 900 ml. of MeOH and 100 ml. of EtOAc in a hydrogenation bottle is added 0.5 g PtO2. The bottle is purged with hydrogen then pressurized to 50 psig and shaken until the required amount of H2 was used. The reaction mixture was filtered through celite, washed well with CH2Cl2 and the combined organic phases concentrated in vacuo to yield 29 g of the product. This product was used without further purification in subsequent transformations.

Workup

  1. customThe bottle is purged with hydrogen
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed well with CH2Cl2
  4. concentrationthe combined organic phases concentrated in vacuo

Sources & evidence

ORD record
ord-6274814401c3424bb806403038c81f40
Source dataset
uspto-grants-1984_03
Patent number
US04439229

Reaction notes

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