Methylamine Acetate → 4-(5-Chloroindol-3-yl)-2-methylamino-4-oxo-2-butenoic acid ethyl ester

HRID 2083873Notes

Reaction equation

HRID 2083873 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5](O)=[CH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[NH:11][CH:10]=1)=[O:8])[CH3:2].C(O)(=O)C.[CH3:25][NH2:26]>CCO>[CH2:1]([O:3][C:4](=[O:20])[C:5]([NH:26][CH3:25])=[CH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[NH:11][CH:10]=1)=[O:8])[CH3:2]

Participants

4

Reactant 2

HCID 13000541Methylamine AcetateHCID 178473094HCID 178473094, compound

Product 1

HCID 600774434-(5-Chloroindol-3-yl)-2-methylamino-4-oxo-2-butenoic acid ethyl esterYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.59 g (2.0 mmol) of 4-(5chloroindol-3-yl)-2-hydroxy-4-oxo-2-butenoic acid ethyl ester prepared in Example 1(1) in 95% EtOH (10 ml) was added 0.55 g (6.0 mmol) of methylamine acetate. After refluxing for 2.5 hours, the reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The ethyl acetate was washed with water, dried, and then concentrated. The resulting residue was chromatographed on silica gel (ethyl acetate as eluant) to give 0.23 g of the titled compound as oil. Yield: 38%.

Workup

  1. temperatureAfter refluxing for 2.5 hours
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe ethyl acetate was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue was chromatographed on silica gel (ethyl acetate as eluant)

Sources & evidence

ORD record
ord-34d02b7ece3c4f959ad3228977aeb796
Source dataset
uspto-grants-2004_04
Patent number
US06716605B2

Reaction notes

Loading…