Sodium Cyanide → HCID 14500523, compound

HRID 1762870Notes

Reaction equation

HRID 1762870 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[C-:16]#[N:17].[Na+]>CN(C=O)C>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:16]#[N:17])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 14500515HCID 14500515, compound

Product 1

HCID 14500523HCID 14500523, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 58.6 g (0.19 mol) of 4-[(6-bromohexyl)amino]phenol from part b in about 400 mL of DMF was added dropwise to a slurry of 46.6 g (0.95 mol) of sodium cyanide in 370 mL of DMF in a 2 L flask at 70° C. over the course of two hours. Heating was continued for two hours. After cooling, the reaction was filtered and diluted with about 2 L of water and extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed three times with saturated sodium chloride solution, and dried over magnesium sulfate. The solution was stripped to a red-orange solid which was dissolved in warm ethyl acetate, treated with decolorizing carbon, cooled, and recrystallized by the addition of a small amount of hexane to yield 7-[(4-hydroxyphenyl)amino]heptanenitrile, mp 75°-76° C., in 53% yield.

Workup

  1. temperatureHeating
  2. temperatureAfter cooling
  3. filtrationthe reaction was filtered
  4. additiondiluted with about 2 L of water
  5. extractionextracted twice with ethyl acetate
  6. washwashed three times with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. dissolutionwas dissolved in warm ethyl acetate
  9. additiontreated with decolorizing carbon
  10. temperaturecooled
  11. customrecrystallized by the addition of a small amount of hexane

Sources & evidence

ORD record
ord-b199ec342a0c4e7ba969b33dd5f11a76
Source dataset
uspto-grants-1989_05
Patent number
US04835180

Reaction notes

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