Sodium Hydroxide → HCID 178420514, compound

HRID 2351879Notes

Reaction equation

HRID 2351879 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]#[N:20].[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C)C=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]1[NH:27][N:26]=[N:25][N:20]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14501728HCID 14501728, compound

Product 1

HCID 178420514HCID 178420514, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8.7 g of 4-[2-(2-quinolylmethyloxy)phenoxy]butyronitrile, 5.3 g of sodium azide and 4.4 g of ammonium chloride is heated with 25 ml of dry dimethylformamide at 140° C. for 20 hours. The reaction mixture is poured onto ice, basified with 1N sodium hydroxide and extracted 2 times with ethyl acetate. The aqueous fraction is acidified with acetic acid. The product is filtered and washed with water. The crude product is crystallized from acetonitrile to give 1.7 g of pure product of M.P. 137°-140° C.

Workup

  1. additionThe reaction mixture is poured onto ice
  2. extractionextracted 2 times with ethyl acetate
  3. filtrationThe product is filtered
  4. washwashed with water
  5. customThe crude product is crystallized from acetonitrile

Sources & evidence

ORD record
ord-59a7103c1f3444ba89dbf126664bdf9a
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

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