HCID 22761659, compound → HCID 22761656, compound

HRID 1703468Notes

Reaction equation

HRID 1703468 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[N:13]1[C:17](=[O:18])[C:16]2=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=[C:15]2[C:14]1=[O:24].[H][H]>[Rh]>[ClH:23].[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[N:13]1[C:17](=[O:18])[C:16]2=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=[C:15]2[C:14]1=[O:24]

Participants

4

Reactant 2

HCID 22761659HCID 22761659, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22761656HCID 22761656, compound

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

The solution of 350 mg of N-(2-methoxymethyl-4-nitrophenyl)-4-chlorophthalimide is hydrogenated over 200 mg of 5% rhodium on carbon at 2.5 atmospheres of hydrogen pressure for 4 hours. After filtration from the catalyst, the residue is refluxed for 24 hours in 5 ml of xylene. After evaporation of the solvent, the residue is dissolved in acetone and the solution neutralized with ethereal hydrogen chloride, to yield the N-(2-methoxymethyl-4-aminophenyl)-4-chlorophthalimide hydrochloride melting at 255°-257°.

Workup

  1. filtrationAfter filtration from the catalyst
  2. temperaturethe residue is refluxed for 24 hours in 5 ml of xylene
  3. customAfter evaporation of the solvent
  4. dissolutionthe residue is dissolved in acetone

Sources & evidence

ORD record
ord-5963800accb44245bfcae20f9cbf4526
Source dataset
uspto-grants-1978_11
Patent number
US04124593

Reaction notes

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