5-Morpholino-2-nitroaniline → 4-(Morpholin-4-yl)benzene-1,2-diamine

HRID 349678Notes

Reaction equation

HRID 349678 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([N+:14]([O-])=O)=[C:11]([NH2:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H][H]>C(O)(=O)C.C(O)C.[Pd]>[N:1]1([C:7]2[CH:12]=[C:11]([NH2:13])[C:10]([NH2:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 5967255-Morpholino-2-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 141123324-(Morpholin-4-yl)benzene-1,2-diamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 5-morpholin-4-yl-2-nitro-phenylamine (4.0 g, 0.02 mol) in acetic acid (100 mL) and ethanol (100 mL) was treated with hydrogen gas (60 psi) for 30 min in the presence of palladium on carbon catalyst (0.5 g, 10% Pd). The catalyst was removed by filtration through CELITE®, and the filtrate was concentrated to a syrup and dried in vacuo to afford the intermediate 4-morpholin-4-yl-benzene-1,2-diamine as a crude green solid (3.2 g).

Workup

  1. customThe catalyst was removed by filtration through CELITE®
  2. concentrationthe filtrate was concentrated to a syrup
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ac74ca14d2064a72aa4797f9e7d3f434
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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