HCID 22761655, compound → HCID 22761649, compound

HRID 1703470Notes

Reaction equation

HRID 1703470 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[N:14]1[C:18](=[O:19])[C:17]2=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=[C:16]2[C:15]1=[O:25])[CH3:2].[H][H]>C(OCC)(=O)C.[Rh]>[CH2:1]([O:3][CH2:4][C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:6]=1[N:14]1[C:18](=[O:19])[C:17]2=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=[C:16]2[C:15]1=[O:25])[CH3:2]

Participants

5

Reactant 2

HCID 22761655HCID 22761655, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22761649HCID 22761649, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 300 mg of N-(2-ethoxymethyl-4-nitrophenyl)-4-chlorophthalimide in 40 ml of ethyl acetate is hydrogenated with 200 mg of 5% rhodium on carbon at 2.5 atmospheres of hydrogen pressure for 3 hours. After filtration from the catalyst the residue is refluxed for 24 hours in 5 ml of xylene, the solution evaporated and the residue crystallized from diethyl ether, to give the N-(2-ethoxymethyl-4-aminophenyl)-4-chlorophthalimide melting at 154°-156°.

Workup

  1. filtrationAfter filtration from the catalyst the residue
  2. temperatureis refluxed for 24 hours in 5 ml of xylene
  3. customthe solution evaporated
  4. customthe residue crystallized from diethyl ether

Sources & evidence

ORD record
ord-93c94b74633d4f7981f863b8167619ab
Source dataset
uspto-grants-1978_11
Patent number
US04124593

Reaction notes

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