4-Aminophenol → 4-(Cinnamoylamino)phenyl 3-phenylacrylate

HRID 655184Notes

Reaction equation

HRID 655184 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.ClCCl.Cl.ClCCl>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:4]1(/[CH:3]=[CH:2]/[C:1]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:1](=[O:10])/[CH:2]=[CH:3]/[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:15][CH:14]=2)=[O:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 4034-AminophenolHCID 6344DichloromethaneHCID 660233-Phenylprop-2-enoyl chlorideHCID 19696284HCl dichloromethane

Product 1

HCID 12345024-(Cinnamoylamino)phenyl 3-phenylacrylateYield 89.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Cinnamoyl chloride (16.79 g, 100.8 mmoL) was added to a solution of 4-aminophenol (5.00 g, 45.8 mmol) and DMAP (0.56 g, 4.58 mmol) in pyridine (50 mL). The reaction mixture was stirred at room temperature for 30 min whereupon a solid mass formed. Dichloromethane (50 mL) was added and the resultant suspension was stirred at room temperature for 2 h. The reaction mixture was poured into 10% hydrochloric acid/dichloromethane and shaken. The precipitated white solid was removed by filtration, washed with dichloromethane, 10% hydrochloric acid and then dichloromethane again. The organic layer of the filtrate was separated and washed with 10% hydrochloric acid (×2) and brine, dried (Na2SO4) and evaporated to give the title compound (15.1 g, 89%). 1HNMR (300 MHz) (CDCl3) δ 6.55 (1H, d, J=16 Hz), 6.64 (1H, d, J=16 Hz), 7.18 (2H, d), 7.35-7.45 (6H, m), 7.58 (4H, m), 7.67 (2H, m), 7.78 (1H, d, J=16) and 7.88 (1H, d, J=16).

Workup

  1. customformed
  2. stirringshaken
  3. customThe precipitated white solid was removed by filtration
  4. washwashed with dichloromethane, 10% hydrochloric acid
  5. customThe organic layer of the filtrate was separated
  6. washwashed with 10% hydrochloric acid (×2) and brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-36e7fac528fd48e3932ae990799efe60
Source dataset
uspto-grants-2011_12
Patent number
US08071582B2

Reaction notes

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