Stannous chloride dihydrate → 4-(Cyclopropylmethoxy)aniline

HRID 1814638Notes

Reaction equation

HRID 1814638 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl>C(O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([NH2:12])=[CH:10][CH:11]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 111715331-(Cyclopropylmethoxy)-4-nitrobenzene

Product 1

HCID 225023114-(Cyclopropylmethoxy)anilineYield 56.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above 4-nitrobenzene (2.0 g, 9.5 mmol) was dissolved in ethanol (50 mL) and tin(II) chloride dihydrate (10.7 g, 48 mmol) was added and the mixture was refluxed for 24 hours. After cooling, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (40 mL) and 1N aqueous sodium hydroxide (180 mL). This mixture was filtered through celite. The aqueous phase was extracted with ethyl acetate (2×50 mL) and the combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford 0.88 g (52%) of 4-cyclopropylmethoxyaniline.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (40 mL)
  5. filtrationThis mixture was filtered through celite
  6. extractionThe aqueous phase was extracted with ethyl acetate (2×50 mL)
  7. dry with materialthe combined organic extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f727d095f5654050a36efed68b5f43ca
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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