Ammonia → Allyl 3-aminocinnamate

HRID 260306Notes

Reaction equation

HRID 260306 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])([O-])=O.O.O.Cl[Sn]Cl.N.O>C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 61436Stannous chloride dihydrateHCID 54426531HCID 54426531, compound

Product 1

HCID 54165426Allyl 3-aminocinnamateYield 99.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

Crude allyl 3-nitrocinnamate (3 g, 12.9 mM) was dissolved in ethyl acetate (10 ml) and added slowly to a stirred suspension of SnCl2.2H2O(14.52 g, 64 mM) in ethyl acetate (20 ml). The mixture was refluxed under argon for 3 hours, cooled, and poured into a mixture of ammonia (sg 880, 15 ml) and water (5 ml). Ethyl acetate (50 ml) was added, and the organic layer separated by decantation. Two further extractions with ethyl acetate (each 50 ml) were made similarly. The combined extracts were washed with water and brine, dried (MgSO4) and evaporated to give title compound (2.6 g).

Workup

  1. temperatureThe mixture was refluxed under argon for 3 hours
  2. temperaturecooled
  3. customthe organic layer separated by decantation
  4. extractionTwo further extractions with ethyl acetate (each 50 ml)
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-2fd70fcadfa24025b57d9499fa9022d8
Source dataset
uspto-grants-1996_06
Patent number
US05527791

Reaction notes

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