HCID 15572629, compound → HCID 13398586, compound

HRID 903966Notes

Reaction equation

HRID 903966 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][CH:7]([CH:14]1[O:19][CH2:18][C:17](=[O:20])[N:16]([CH3:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-])=O>CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][CH:7]([CH:14]1[O:19][CH2:18][C:17](=[O:20])[N:16]([CH3:21])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 15572629HCID 15572629, compound

Product 1

HCID 13398586HCID 13398586, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7 g of 2-[α-(2-nitro-phenoxy)-benzyl]-4-methyl-morpholin-5-one in 200 ml of DMF, 5% Palladium-charcoal (0.7 g) was added and the mixture was hydrogenated at 3.5 atmospheres for 0.5 hours. The catalyst was filtered off, the solution was poured into water and then extracted with ethyl acetate. After anhydrification and evaporation to dryness of the solvent, crystallization from ethyl ether gave 2-[α-(2-amino-phenoxy)-benzyl]-4-methyl-morpholin-5-one, m.p. 167°-170° C. (5.3 g; 75.2%).

Workup

  1. filtrationThe catalyst was filtered off
  2. additionthe solution was poured into water
  3. extractionextracted with ethyl acetate
  4. customAfter anhydrification and evaporation
  5. customto dryness of the solvent, crystallization from ethyl ether

Sources & evidence

ORD record
ord-df24f739a91846c6bff806b0eac702c1
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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