Acetic Acid → 3-(5-Fluoro-2-methoxy-phenylamino)-but-2-enoic acid ethyl ester

HRID 1959546Notes

Reaction equation

HRID 1959546 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([NH2:8])[CH:7]=1.[CH2:11]([O:13][C:14](=[O:19])[CH2:15][C:16](=O)[CH3:17])[CH3:12].C(O)(=O)C.[O-]S([O-])(=O)=O.[Ca+2]>C(O)C>[CH2:11]([O:13][C:14](=[O:19])[CH:15]=[C:16]([NH:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:9][CH3:10])[CH3:17])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 24497Calcium SulfateHCID 2231055-Fluoro-2-methoxyaniline

Product 1

HCID 670780423-(5-Fluoro-2-methoxy-phenylamino)-but-2-enoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-fluoro-2-methoxy-phenylamine (3.3 g, 23 mmol), 3-oxo-butyric acid ethyl ester (3.0 g, 23 mmol), acetic acid (120 μL), and Drierite® (12.0 g) in ethanol (20 mL) was heated to reflux for 5 d. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography on silica gel (elution with EA/hexane 1:3) to give crude 3-(5-fluoro-2-methoxy-phenylamino)-but-2-enoic acid ethyl ester.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 d
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by flash chromatography on silica gel (elution with EA/hexane 1:3)

Sources & evidence

ORD record
ord-f4042b31147f4363a8cb35246c454bf0
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

Loading…