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

HRID 2378718Notes

Reaction equation

HRID 2378718 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-f0902de9772741c9a7374aa3f6ed398c
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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