Hydrochloric Acid → (2E)-3-[4-(tert-Butyl)phenyl]-N-(3-hydroxyphenyl)prop-2-enamide

HRID 2105563Notes

Reaction equation

HRID 2105563 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[NH2:22][C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[K+].[K+].Cl>C1COCC1.CN(C=O)C.C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8](/[CH:9]=[CH:10]/[C:11]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=2)=[O:13])=[CH:14][CH:15]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 65578Oxalyl chlorideHCID 7248394-(Tert-butyl)cinnamic acid

Product 1

HCID 10214883(2E)-3-[4-(tert-Butyl)phenyl]-N-(3-hydroxyphenyl)prop-2-enamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a round-bottomed flask equipped with magnetic stirring was added 4-tert-butyl-trans-cinnamic acid (530 mg, 2.43 mmol, EMKA-Chemie), CH2Cl2 (10 mL), and DMF (10 uL, Aldrich) under N2. The solution was treated dropwise with oxalyl chloride (3.0 mL, 6.0 mmol, 2.0 M in CH2Cl2, Aldrich) then stirred at 25° C. for 1 h. The reaction mixture was concentrated in vacuo and treated with 3-aminophenol (265 mg, 2.43 mmol, Aldrich), THF (20 mL) and satd K2CO3 (15 mL). The reaction mixture was stirred at 25° C. overnight, then acidified to pH˜4.5 with 1 N HCl. The mixture was extracted with EtOAc (2×30 mL), the combined organic extract was dried and concentrated in vacuo. Purification by silica gel chromatography (2:1 hexane:EtOAc) provided the title product as an oil. MS (ESI, pos. ion) m/z: 296 (M+1).

Workup

  1. customTo a round-bottomed flask equipped
  2. stirringthen stirred at 25° C. for 1 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. stirringThe reaction mixture was stirred at 25° C. overnight
  5. extractionThe mixture was extracted with EtOAc (2×30 mL)
  6. extractionthe combined organic extract
  7. customwas dried
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel chromatography (2:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-b37ffd9972954f5d92e088d6184b3338
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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