Water → 1-Amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene

HRID 1596750Notes

Reaction equation

HRID 1596750 reaction equation
C[N:2](C)C=O.[CH3:6][O:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[O:19])=[CH:12][CH:11]=1)=[O:9].C([O-])(=O)C.[NH4+].O>C(OCC)(=O)C>[NH2:2][C:16]([C:13]1[CH:14]=[CH:15][C:10]([C:8]([O:7][CH3:6])=[O:9])=[CH:11][CH:12]=1)=[CH:17][C:18](=[O:19])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 517165Ammonium AcetateHCID 11405985Methyl 4-[1,3-dioxo-3-[4-(pentyloxy)phenyl]propyl]benzoate

Product 1

HCID 696777131-Amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dimethylformamide (50 ml), 1-(4-methoxycarbonyl-phenyl)-3-(4-pentyloxyphenyl)propane-1,3-dione (10.0 g) and ammonium acetate (9.9 g) were charged in 500-ml three-necked flask at room temperature and heated, and the reaction was carried out at the inner temperature of 90 to 100 ° C. for 4 hours. After completion of the reaction, the mixture was cooled down to room temperature, water (250 ml) and ethyl acetate (250 ml) were added, the mixture was stirred, and an ethyl acetate layer was separated. The ethyl acetate layer was further washed with water (250 ml) and a saturated saline solution (100 ml). The ethyl acetate layer was concentrated in vacuo to make 50 ml, and n-heptane (250 ml) was added to separate crystals of 1-amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene. The crystals were filtered at room temperature and washed with a solution (50 ml) consisting of n-heptane and ethyl acetate (5:1). The crystals were dried overnight in vacuo and purified by suspending in a 70% aqueous acetone (100 ml) to give 1-amino-1-(4-methoxycarbonyl-phenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene (6.56 g).

Workup

  1. temperatureheated
  2. customAfter completion of the reaction
  3. customan ethyl acetate layer was separated
  4. washThe ethyl acetate layer was further washed with water (250 ml)
  5. concentrationThe ethyl acetate layer was concentrated in vacuo
  6. additionwas added
  7. customto separate crystals of 1-amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene
  8. filtrationThe crystals were filtered at room temperature
  9. washwashed with a solution (50 ml)
  10. customThe crystals were dried overnight in vacuo
  11. custompurified

Sources & evidence

ORD record
ord-e1bcc010cc0849c69c8846c3431e5234
Source dataset
uspto-grants-2001_09
Patent number
US06291680B1

Reaction notes

Loading…