Ethyl Acetoacetate → Ethyl 3-[4-(benzyloxy)anilino]but-2-enoate

HRID 408647Notes

Reaction equation

HRID 408647 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:17][C:18]([CH3:20])=O>>[CH2:23]([O:22][C:16](=[O:21])[CH:17]=[C:18]([NH:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:15][CH:14]=1)[CH3:20])[CH3:24]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 228604-Benzyloxyaniline

Product 1

HCID 68726629Ethyl 3-[4-(benzyloxy)anilino]but-2-enoateYield 49.9%

Procedure

4-Benzyloxyaniline (10 g) and ethyl acetoacetate (6.9 g) were heated at 120° C. for 3 hours. The residue was purified by chromatography on silica eluting with a mixture of dichloromethane, and pentane. The desired fractions were concentrated and the sample evaporated to give the sub-title compound (7.8 g).

Workup

  1. customThe residue was purified by chromatography on silica eluting with a mixture of dichloromethane, and pentane
  2. concentrationThe desired fractions were concentrated
  3. customthe sample evaporated

Sources & evidence

ORD record
ord-9ab06209a42043369fc51d09ffedcba8
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

Loading…