Sodium Hydroxide → HCID 178420514, compound

HRID 1904681Notes

Reaction equation

HRID 1904681 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 was heated with 25 ml of dry dimethylformamide at 140° C. for twenty hours. The reaction mixture was poured onto ice, basified with 1N sodium hydroxide and extracted 2 times with ethyl acetate. The aqueous fraction was acidified with acetic acid. The product was filtered and washed with water. The crude product was crystallized from acetonitrile to give 1.7 g of pure product of m.p. 137°-140° C.

Workup

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

Sources & evidence

ORD record
ord-f477394cddd3497fab928f3a1c290bc3
Source dataset
uspto-grants-1989_06
Patent number
US04839369

Reaction notes

Loading…