Acetonitrile → HCID 13020125, compound

HRID 867090Notes

Reaction equation

HRID 867090 reaction equation
[C:1](#[N:3])[CH3:2].C([Li])CCC.BrC1C=CC([C:16]2[C:21]([C:22]([C:24]3[C:25]([C:30]4[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][CH:31]=4)=NC=CC=3)=O)=CC=[CH:18][N:17]=2)=CC=1.C(Cl)Cl.[O:40]1CCCC1>CCCCCC>[Br:36][C:33]1[CH:32]=[CH:31][C:30]([C:25]([OH:40])([C:24]2[CH:18]=[N:17][CH:16]=[CH:21][CH:22]=2)[CH2:2][C:1]#[N:3])=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 8028Tetrahydrofuran3×HCID 53446548HCID 53446548, compoundHCID 178418339Butyllithium

Product 1

HCID 13020125HCID 13020125, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 6.5 g (0.16 mole) of acetonitrile and 50 ml of dry tetrahydrofuran (THF) was slowly added under N2 -atm to a mixture of 100 ml of 1.5 M n-butyllithium in hexane and 50 ml of dry THF at -50° C. After stirring for 35 minutes a solution of 36.5 g (0.14 mole) of 4-bromophenyl-3-pyridylketone in 250 ml of dry THF was added at -50° C. The temperature was kept at -70° C. for 15 minutes, then the reaction mixture became viscous and it was allowed to reach ambient temperature. The product was poured into a stirred mixture of 500 g of icewater and 500 ml of methylene chloride. The layers were separated and the aqueous layer was extracted with 2×200 ml of CH2Cl2. The combined organic layers were washed with water and dried. The solvent was evaporated giving 39.7 g of an oil. It was dissolved in 550 ml of hot i-PrOH and a solution of 35 ml of 4M HCl-ether (0.14 mole) in 100 ml of i-PrOH was added. After cooling there was collected 34.6 g (74%) of the hydrochloride of 3-(4-bromophenyl)-3-hydroxy-3-(3-pyridyl)-propionitrile. M.p. 158°-161° C. ##STR33##

Workup

  1. additionwas added at -50° C
  2. customto reach ambient temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with 2×200 ml of CH2Cl2
  5. washThe combined organic layers were washed with water
  6. customdried
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-22916579757a429bbedaa020683db59d
Source dataset
uspto-grants-1978_07
Patent number
US04102887

Reaction notes

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