Sodium Chloride → HCID 10486994, compound

HRID 648003Notes

Reaction equation

HRID 648003 reaction equation
I[CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][C:11]#[N:12].[H-].[Na+].CCCCCC.C(OCC)(=O)C.[Cl-].[Na+]>CN(C)C=O>[C:11]([CH:10]1[CH2:2][CH2:3][CH2:4][N:5]2[CH:9]=[CH:8][CH:7]=[C:6]12)#[N:12]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 20484071HCID 20484071, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 10486994HCID 10486994, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-Iodopropyl)pyrrol-2-acetonitrile (31 g., 0.128 moles) is dissolved in dry dimethylformanide (35 ml.) is added with stirring to a cooled (-5°) suspension of sodium hydride (50%, 7.5 g., 0.156 moles) in dry dimethylformamide (100 ml.), maintained in an atmosphere of dry nitrogen, at a rate such that the reaction temperature is maintained between -5° to +5°. When the addition is completed, stirring at this temperature is continued for 1 hour at which time the starting material is shown to be absent by t.l.c. (silica gel, hexane-ethyl acetate, 1:1). A cold, dilute solution of sodium chloride (150 ml.) is added to the reaction during 15 minutes and the product is extracted into benzene. The extract is washed with dilute sodium chloride solution (3 times), with water (once) and then it is dried over sodium sulfate. The solvent is removed in vacuo leaving an oil (21.1 g.) which is chromatographed on silica gel. The crystalline product (13.6 g., 72%) is eluted with hexane-ethyl acetate (97.5:25 and 95:5). Crystallization from hexane-acetone yields 8-cyano-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine (XIX, n is 1), m.p. 47°-49°.

Workup

  1. additionis added
  2. temperaturea cooled
  3. temperaturemaintained in an atmosphere of dry nitrogen, at a rate such that the reaction temperature
  4. temperatureis maintained between -5° to +5°
  5. additionWhen the addition
  6. stirringstirring at this temperature
  7. extractionthe product is extracted into benzene
  8. washThe extract is washed with dilute sodium chloride solution (3 times), with water (once) and then it
  9. dry with materialis dried over sodium sulfate
  10. customThe solvent is removed in vacuo
  11. customleaving an oil (21.1 g.) which
  12. customis chromatographed on silica gel
  13. washThe crystalline product (13.6 g., 72%) is eluted with hexane-ethyl acetate (97.5:25 and 95:5)
  14. customCrystallization from hexane-acetone

Sources & evidence

ORD record
ord-d621d145542a4cecbb0992448a33865f
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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