Morpholine, 4-(2,4-dinitrophenylbenzoyl)- → N-(2,4-diaminobenzoyl)morpholine

HRID 2108147

Reaction equation

HRID 2108147 reaction equation
[N+:1]([C:4]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:5]=1[C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7])([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:5]=1[C:6]([N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)=[O:7]

Participants

5

Reactant 2

HCID 544864Morpholine, 4-(2,4-dinitrophenylbenzoyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 19817762N-(2,4-diaminobenzoyl)morpholineYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A two liter autoclave was charged with 130.6 g of N-(2,4-dinitrobenzoyl)morpholine, 1200 ml methanol and 6.2 g of a 5% palladium on carbon/50% water catalyst. The mixture was hydrogenated at 800 psi while maintaining the temperature between 60°-100° C. Hydrogen uptake ceased after 30 min. The mixture was cooled, filtered and methanol removed at reduced pressure. The residue was crystallized from toluene to yield 97.1 g of N-(2,4-diaminobenzoyl)morpholine, mp 114°-115° C.

Workup

  1. temperaturewhile maintaining the temperature between 60°-100° C
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. custommethanol removed at reduced pressure
  5. customThe residue was crystallized from toluene

Sources & evidence

ORD record
ord-956e158c31314d929f303d6dcf49add1
Source dataset
uspto-grants-1990_06
Patent number
US04937306

Linked notes

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