Triethylamine → HCID 178499206, compound

HRID 2180907Notes

Reaction equation

HRID 2180907 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:15][O:16][C:17]([C:19]1([O:28][CH3:29])[CH2:24][CH:23]([CH3:25])[C:22](=[O:26])[CH:21]=[C:20]1[OH:27])=[O:18].C(N(CC)CC)C.[C-]#N.[K+]>C(#N)C>[CH3:15][O:16][C:17]([C:19]1([O:28][CH3:29])[CH2:24][CH:23]([CH3:25])[C:22](=[O:26])[C:21]([C:4]([C:3]2[C:2]([CH3:1])=[N:10][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:8][CH:7]=2)=[O:5])=[C:20]1[OH:27])=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 27756752-Methyl-6-(trifluoromethyl)nicotinoyl chlorideHCID 18755506Methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate

Product 1

HCID 178499206HCID 178499206, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.23 g of fresh 2-methyl-6-trifluoromethyl-nicotinoyl chloride are added to a mixture of 2.14 g of 2-hydroxy-1-methoxy-5-methyl-4-oxo-cyclohex-2-ene-carboxylic acid methyl ester and 2.02 g of triethylamine in 30 ml of acetonitrile. After about 30 minutes, 0.065 g of potassium cyanide is added and the batch is stirred for 18 hours. The batch is then extracted at pH 2 with water against ethyl acetate, dried over magnesium sulfate and concentrated by evaporation. By filtering over silica gel (mobile phase: ethyl acetate/methanol/triethylamine 85:10:5), pure 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)-4-oxo-cyclohex-2-enecarboxylic acid methyl ester is obtained in the form of a viscous oil.

Workup

  1. extractionThe batch is then extracted at pH 2 with water against ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated by evaporation
  4. filtrationBy filtering over silica gel (mobile phase: ethyl acetate/methanol/triethylamine 85:10:5)

Sources & evidence

ORD record
ord-add1cba9930a426587a21461944fea68
Source dataset
uspto-grants-2005_05
Patent number
US06890885B2

Reaction notes

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