4-Dimethoxymethyl-1-(2-morpholinoethoxy)-2-nitrobenzene → 5-Dimethoxymethyl-2-(2-morpholinoethoxy)aniline

HRID 2075435Notes

Reaction equation

HRID 2075435 reaction equation
[CH3:1][O:2][CH:3]([O:22][CH3:23])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[C:6]([N+:19]([O-])=O)[CH:5]=1>C(O)C.[Pt]=O>[CH3:1][O:2][CH:3]([O:22][CH3:23])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[C:6]([CH:5]=1)[NH2:19]

Participants

4

Reactant 1

HCID 231179024-Dimethoxymethyl-1-(2-morpholinoethoxy)-2-nitrobenzene

Product 1

HCID 231179015-Dimethoxymethyl-2-(2-morpholinoethoxy)anilineYield 26%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 4-dimethoxymethyl-1-(2-morpholinoethoxy)-2-nitrobenzene obtained in Step 2 (2.97 g, 9.10 mmol) in ethanol (30.0 mL) was added with platinum oxide (0.02 g, 0.10 mmol), followed by stirring at room temperature under hydrogen atmosphere for 2 hours. The reaction mixture was filtered, the solvent of filtrate was evaporated under reduced pressure, the resulting crude product was crystallized from mixed solvent of ethyl acetate/hexane (1/1) to obtain 5-dimethoxymethyl-2-(2-morpholinoethoxy)aniline (0.70 g, 26%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent of filtrate was evaporated under reduced pressure
  3. customthe resulting crude product was crystallized
  4. additionfrom mixed solvent of ethyl acetate/hexane (1/1)

Sources & evidence

ORD record
ord-100f39a7f3a647ea8e94749e334180b8
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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