Stannous chloride dihydrate → Allyl 3-allyloxy-4-aminobenzoate

HRID 1736356Notes

Reaction equation

HRID 1736356 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])[CH:2]=[CH2:3].O.O.Cl[Sn]Cl.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][C:16]=1[NH2:17])[C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 19432478Allyl 3-allyloxy-4-nitrobenzoate

Product 1

HCID 19432469Allyl 3-allyloxy-4-aminobenzoateYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The crude ester (10 g, 38 mM) was dissolved in ethanol (20 ml) and added to a stirred suspension of SnCl2.2H2O (42.9 g, 0.19M) in ethanol (60 ml) under argon at ambient temperature. The mixture was heated to reflux for 30 minutes, cooled and poured onto ice. After making basic to pH 8 with an aqueous solution of sodium bicarbonate, the mixture was extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over MgSO4 and evaporated to give allyl 3-allyloxy-4-aminobenzoate (8.2 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturecooled
  4. additionpoured onto ice
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-083fff70d481497c8a807698a4114f35
Source dataset
uspto-grants-1996_07
Patent number
US05541178

Reaction notes

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