2,6-Dichlorobenzaldehyde → HCID 70204165, compound

HRID 342507Notes

Reaction equation

HRID 342507 reaction equation
[NH2:1][C:2]([CH3:11])=[CH:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:14]=1[CH:15]=O.[CH3:22][O:23][C:24]([CH2:26][C:27]([CH2:29][C:30]([O:32][CH3:33])=[O:31])=O)=[O:25]>CO>[C:7]([O:6][C:4]([C:3]1[CH:15]([C:14]2[C:13]([Cl:12])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:21])[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:27]([CH2:26][C:24]([O:23][CH3:22])=[O:25])[NH:1][C:2]=1[CH3:11])=[O:5])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 74591Dimethyl 3-oxoglutarateHCID 558169tert-Butyl 3-aminobut-2-enoate

Product 1

HCID 70204165HCID 70204165, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of t-butyl 3-amino-2-butenoate (3.911 g, 24.8 mmol), 2,6-dichlorobenzaldehyde (4.354 g, 24.8 mmol), and dimethyl acetonedicarboxylate (3.657 ml, 24.8 mmol) in methanol (50 ml) was refluxed for 45 h. The solvent was evaporated and the residue was chromatographed on 800 g silica gel (dichloromethane/ethyl acetate: 23/2 as eluent) to give 1.18 g of product. On silica GF plates, the product was blue fluorescent at Rf=0.3.

Workup

  1. temperaturewas refluxed for 45 h
  2. customThe solvent was evaporated
  3. customthe residue was chromatographed on 800 g silica gel (dichloromethane/ethyl acetate: 23/2 as eluent)

Sources & evidence

ORD record
ord-7ff7d96be05f4f74a19a2a3299e2a809
Source dataset
uspto-grants-1999_01
Patent number
US05859011

Reaction notes

Loading…