HCID 9899728, compound → HCID 86682382, compound

HRID 1465831Notes

Reaction equation

HRID 1465831 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[CH:9]=[CH:10][C:11]([N+:15]([O-])=O)=[C:12]([CH:14]=2)[NH2:13])[CH2:5][C@@H:4]([CH3:18])[O:3]1>[Pd].C(OCC)(=O)C.CO>[NH2:13][C:12]1[CH:14]=[C:8]([N:6]2[CH2:5][C@@H:4]([CH3:18])[O:3][C@@H:2]([CH3:1])[CH2:7]2)[CH:9]=[CH:10][C:11]=1[NH2:15]

Participants

4

Reactant 1

HCID 9899728HCID 9899728, compound

Product 1

HCID 86682382HCID 86682382, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 5-(cis-2′,6′-dimethylmorpholino)-2-nitroaniline (1.26 g, 5.03 mmol) in 4:1 ethyl acetate/methanol (75 ml) was added 5% palladium on carbon (0.24 g) and the reaction mixture stirred under an atmosphere of hydrogen for 25 h. The reaction mixture was then filtered through celite, the filtered solid washed with methanol, and the combined filtrate and washings concentrated in vacuo to give crude 2-amino-4-(cis-2′,6′-dimethylmorpholino)aniline (1.08 g, 97%) which was used immediately in the next step.

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. washthe filtered solid washed with methanol
  3. concentrationthe combined filtrate and washings concentrated in vacuo

Sources & evidence

ORD record
ord-3d1e82caa1224710bf59ff31808281d8
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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