Hydrochloric Acid → HCID 20342251, compound

HRID 2050184Notes

Reaction equation

HRID 2050184 reaction equation
[C:1]([N:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[CH:14]=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:16]#[N:17].[K+].Cl>O1CCCC1.O>[OH:15][CH:14]([CH:10]1[CH2:11][CH2:12][CH2:13][N:9]1[C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:16]#[N:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 14824833HCID 14824833, compound

Product 1

HCID 20342251HCID 20342251, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.347 g (16.5 mmoles) of 1-benzoyl-2-formylpyrrolidine in a mixture of 28 ml of tetrahydrofuran and 19 ml of water are added 1.30 g (20 mmoles; 1.23 equivalents) of potassium cyanide and 1.4 ml (16.7 mmoles) of concentrated hydrochloric acid. After 1 hour, the mixture is diluted with water and extracted with chloroform. The organic layer is separated, washed with water, dried over sodium sulfate, and evaporated under reduced pressure to yield 3.8 g of crude crystalline 2-hydroxy-2-(1-benzoylpyrrolidin-2-yl)acetonitrile in quantitative yield.

Workup

  1. extractionextracted with chloroform
  2. customThe organic layer is separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-219b46444eff45c4826de78672f90cac
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Reaction notes

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