Tetrahydrofuran → HCID 85549802, compound

HRID 1252702Notes

Reaction equation

HRID 1252702 reaction equation
C([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5](CC)[N:4]=1)C.[C:14]1([O:20][C:21](Cl)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:24]1([Mg]Br)C=CC=C[CH:25]=1.O1CC[CH2:34][CH2:33]1>C(OCC)C.[Cu]I>[CH2:24]([N:9]([CH2:33][CH3:34])[C:7]([C:6]1[CH2:10][CH:11]=[CH:3][N:4]([C:21]([O:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:22])[CH:5]=1)=[O:8])[CH3:25]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 15891Phenyl chloroformateHCID 14393054HCID 14393054, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 85549802HCID 85549802, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-20 °C

Procedure

To a mixture of diethylnicotinamide (3.56 g, 0.02 mol) and copper(I) iodide (3.8 g, 0.02 mol) in 50 ml of tetrahydrofuran was added 3.12 g (0.02 mol) of phenylchloroformate at -20° C. After addition was complete, the mixture was stirred at -20° C. for 15 minutes. Phenylmagnesium bromide (6-9 ml of a 2.9 M solution in diethyl ether) was added to the reaction mixture in a dropwise manner. This mixture was stirred at ambient temperature overnight, and then quenched with a 20% aqueous ammonium chloride solution. Diethyl ether was added, and the organic layer was separated, washed successively with 20% aquous solution of 1:1 ammonium chloride/ammonia solution, water, 10% aqueous HCl, again with water, and finally with brine solution. The organic solution was then dried and evaporated to yield 3-[(diethylamino)carbonyl]-1(4H)-pyridinecarboxylic acid, phenyl ester as a yellow oil.

Workup

  1. additionAfter addition
  2. stirringThis mixture was stirred at ambient temperature overnight
  3. customquenched with a 20% aqueous ammonium chloride solution
  4. additionDiethyl ether was added
  5. customthe organic layer was separated
  6. washwashed successively with 20% aquous solution of 1:1 ammonium chloride/ammonia solution, water, 10% aqueous HCl, again with water
  7. customThe organic solution was then dried
  8. customevaporated

Sources & evidence

ORD record
ord-68f2a530efd84a019f46d4abbdf78c89
Source dataset
uspto-grants-1988_05
Patent number
US04745123

Reaction notes

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