Stannous chloride dihydrate → Allyl 3-aminophenoxyacetate

HRID 260309Notes

Reaction equation

HRID 260309 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])([O-])=O.O.O.Cl[Sn]Cl.[BH4-].[Na+]>C(OCC)(=O)C.C(O)(C)(C)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 4311764Sodium borohydrideHCID 22401165Allyl 3-nitrophenoxyacetate

Product 1

HCID 22401151Allyl 3-aminophenoxyacetateYield 59.8%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Allyl 3-nitrophenoxyacetate (5 g, 0.021M) was dissolved in a mixture of ethyl acetate (45 ml) and t-butanol (5 ml), and SnCl2.2H2O (23.79 g, 0.105M) added. After stirring and heating at 60° for 1 hour, sodium borohydride (399 mg, 0.0105M) was added in portions, and heating continued for another 2 hours. Solvent was removed, the residue was taken up in water, and the pH adjusted to 7.6 with aqueous NaHCO3. Organics were extracted into ethyl acetate, and the combined organic layers washed with aqueous NaHCO3, water, brine, and dried (MgSO4). Evaporation gave the title compound (2.61 g).

Workup

  1. additionadded
  2. temperatureheating at 60° for 1 hour
  3. temperatureheating
  4. customSolvent was removed
  5. extractionOrganics were extracted into ethyl acetate
  6. washthe combined organic layers washed with aqueous NaHCO3, water, brine
  7. dry with materialdried (MgSO4)
  8. customEvaporation

Sources & evidence

ORD record
ord-50b4d048dc3c469789fd5a4ab7b11d1c
Source dataset
uspto-grants-1996_06
Patent number
US05527791

Reaction notes

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