(3,4-Dinitrophenyl)(morpholino)methanone → (3,4-diaMinophenyl)(Morpholino)Methanone

HRID 1946240Notes

Reaction equation

HRID 1946240 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[CH:7]=[CH:8][C:9]=1[NH2:10]

Participants

4

Reactant 1

HCID 13043973(3,4-Dinitrophenyl)(morpholino)methanone

Product 1

HCID 22411123(3,4-diaMinophenyl)(Morpholino)MethanoneYield 114.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (3,4-dinitro-phenyl)-morpholin-4-yl-methanone (1.0 g) and 10% Pd/C (150 mg) in MeOH (30 ml) was shaken under a hydrogen atmosphere at ambient temperature for 10 hours, then filtered through a plug of Celite and reduced in vacuo to give (3,4-diamino-phenyl)-morpholin-4-yl-methanone (900 mg). (1H NMR (300 MHz, DMSO-d6) δ 6.6 (s, 1H), 6.5 (s, 2H), 4.8 (s, 1.5H), 4.6 (s, 1.5H), 4.1 (s, 1H), 3.6 (m, 4H), 3.4 (m, 4H)).

Workup

  1. filtrationfiltered through a plug of Celite

Sources & evidence

ORD record
ord-a6c42cbf0196468cb3fe4e27d93aaf2c
Source dataset
uspto-grants-2013_03
Patent number
US08399442B2

Reaction notes

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