Acrylic Acid → HCID 15086626, compound

HRID 359095Notes

Reaction equation

HRID 359095 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:23]([OH:27])(=[O:26])[CH:24]=[CH2:25]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:23]([CH2:24][CH2:25][N:8]([CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1)[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)([OH:27])=[O:26]

Participants

5

Reactant 2

HCID 6581Acrylic AcidHCID 14882805HCID 14882805, compound

Product 1

HCID 15086626HCID 15086626, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 4-[3-[N-[4-chlorophenyl)amino]propoxy]benzoate (2.0 g) was dissolved in toluene (6 ml), and thereto was added acrylic acid (2.24 ml), and the mixture was heated with stirring at 100° C. for 24 hours. The reaction mixture was diluted with ethyl acetate, and washed successively with aqueous sodium bicarbonate solution 2 times and water once, and it was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixed solvent of chloroform/methanol [60:1 (v/v)] to give the oily desired product (1.64 g).

Workup

  1. temperaturethe mixture was heated
  2. washwashed successively with aqueous sodium bicarbonate solution 2 times and water once
  3. concentrationit was concentrated under reduced pressure
  4. washeluted with a mixed solvent of chloroform/methanol [60:1 (v/v)]

Sources & evidence

ORD record
ord-499395a7b9f94effacead430de9dda5f
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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