Pyridine → N-(1-Acetyl-but-3-enyl)-4-methoxy-benzamide

HRID 479141Notes

Reaction equation

HRID 479141 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][CH:10]([CH2:14][CH:15]=[CH2:16])[C:11]([OH:13])=O)=[O:8])=[CH:5][CH:4]=1.N1C=CC=C[CH:20]=1.CC(OC(C)=O)=O>O>[C:11]([CH:10]([NH:9][C:7](=[O:8])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=1)[CH2:14][CH:15]=[CH2:16])(=[O:13])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 180035572-(4-Methoxy-benzoylamino)-pent-4-enoic acid

Product 1

HCID 18003598N-(1-Acetyl-but-3-enyl)-4-methoxy-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8.41 g of the above prepared 2-(4-methoxy-benzoylamino)-pent-4-enoic acid (33.7 mmol) was added successively 21.2 ml of pyridine and 15.95 ml of Ac2O (5 eq.). The reaction mixture was then kept for 45 min. at 90°. After cooling, 15.8 ml of water was added and the mixture again kept for 30 min. at 85° to ensure complete hydrolysis. Afterwards, it was poured onto crashed ice/HCl, extracted twice with AcOEt, washed with 2N HCl and water, and dried over natrium sulfate. Evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=7/3) afforded 6.45 g of the title compound as yellow solid of mp. 58-59°.

Workup

  1. temperatureAfter cooling
  2. waitthe mixture again kept for 30 min. at 85°
  3. customhydrolysis
  4. additionAfterwards, it was poured
  5. extractionextracted twice with AcOEt
  6. washwashed with 2N HCl and water
  7. dry with materialdried over natrium sulfate
  8. customEvaporation of the solvents

Sources & evidence

ORD record
ord-ef95d081113d4f7f8f175604c3cda0d3
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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