Stannous chloride dihydrate → 4-Methoxy-3-[2-(morpholin-4-yl)ethoxy]aniline

HRID 2174480Notes

Reaction equation

HRID 2174480 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.O.O.[Sn](Cl)Cl>CCO>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 22496148HCID 22496148, compound

Product 1

HCID 186726704-Methoxy-3-[2-(morpholin-4-yl)ethoxy]anilineYield 47.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4-(2-(2-methoxy-5-nitrophenoxy)ethyl)morpholine (350 mg, 1.2 mmol, 1 eq.) and tin (II) chloride dihydrate (1.4 g, 6.20 mmol, 5 eq.) were placed in EtOH (12.3 mL). The reaction mixture was heated at 60° C. and stirred for 19 hours. The reaction mixture was then concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was washed with a 1N NaOH aqueous solution, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 4-methoxy-3-(2-morpholinoethoxy)aniline (143 mg, 46%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washThe organic phase was washed with a 1N NaOH aqueous solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7889e8994b76452eb68ab2fd6174dde1
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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