Dimethylformamide → HCID 13984001, compound

HRID 568938Notes

Reaction equation

HRID 568938 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:18])=[CH:5][C:6](=[O:17])[C:7]=1[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9].[CH3:19][CH2:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])=[C:6]([O:17][CH2:19][CH2:20][CH3:21])[CH:5]=[C:4]([CH3:18])[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 20138780HCID 20138780, compound

Product 1

HCID 13984001HCID 13984001, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.42 (10 m mol) of 1,4-dihydro-2,6-dimethyl-4-oxo-N-phenyl-3-pyridinecarboxamide, 1.84 g (15 m mol) of n-propyl bromide, 1.52 g (11 m mol) of potassium carbonate and 40 ml of N,N-dimethylformamide was stirred for 7 hours at 90° C. (bath temperature). About 100 ml of water was added to the reaction mixture. The mixture was cooled to room temperature to precipitate crystals. The crystals were filtered off, washed and dried under reduced pressure to obtain 2.14 g of 2,6-dimethyl-N-phenyl-4-propoxy-3-pyridinecarboxamide

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customto precipitate crystals
  3. filtrationThe crystals were filtered off
  4. washwashed
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-2ea30115585842ff9dbd8e1108a96f51
Source dataset
uspto-grants-1988_03
Patent number
US04730051

Reaction notes

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