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

HRID 1047558Notes

Reaction equation

HRID 1047558 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([N+:14]([O-])=O)=[C:11]([CH:13]=2)[NH2:12])[CH2:3][CH2:2]1.[H][H]>C(O)C.[Pd]>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:13]=[C:11]([NH2:12])[C:10]([NH2:14])=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

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

Product 1

HCID 141123324-(Morpholin-4-yl)benzene-1,2-diamineYield 86.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Morpholino-2-nitroaniline (200 mg, 0.896 mmol) was added to the 10% Pd/C (25 mg) in ethanol (25 mL) and then hydrogen gas (60 psi) was applied for overnight at room temperature. The reaction mixture was filtered through Celite, and the solvent was removed in vacuum. Purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound (150 mg). 1H NMR: (400 MHz, DMSO-d6): δ 6.38 (d, 1H, J=8.0 Hz), 6.18 (d, 1H, J=2.4 Hz), 5.99 (dd, 1H, J=2.4 and 8.4 Hz), 4.35 (bs, 2H), 3.97 (bs, 2H), 3.66 (m, 4H), 2.81 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed in vacuum
  3. customPurification by flash chromatography (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-c325b2725cb747b3a7ec2170d4538f15
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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