Potassium Carbonate → N-allyl-N-(4-methoxyphenyl)acrylamide

HRID 562577Notes

Reaction equation

HRID 562577 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+].[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>C(Cl)Cl>[CH2:1]([N:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[C:19](=[O:22])[CH:20]=[CH2:21])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13140Acryloyl chlorideHCID 294496N-Allyl-P-anisidine,tech.

Product 1

HCID 67006926N-allyl-N-(4-methoxyphenyl)acrylamideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-allyl-4-methoxyaniline (1.00 g, 6.13 mmol) in methylene chloride (20 mL) was added K2CO3 (2.12 mg, 15.3 mmol) and acryloyl chloride (548 μL, 6.74 mmol) at 0° C. After 15 min., the reaction was quenched with NaHCO3 (5 mL, sat. aq.) and the organic layer was isolated, concentrated and subjected to flash chromatography (Hexanes:EtOAc 4:1) to yield N-allyl-N-(4-methoxyphenyl)acrylamide (1.29 mg, 97%).

Workup

  1. customthe reaction was quenched with NaHCO3 (5 mL, sat. aq.)
  2. customthe organic layer was isolated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b0a5e65cd8714ebf9680a1454527ca05
Source dataset
uspto-grants-2011_11
Patent number
US08067415B2

Reaction notes

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