Sodium Hydroxide → HCID 178420714, compound

HRID 1904673Notes

Reaction equation

HRID 1904673 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[O:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)#[N:2].[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C)C=O>[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[CH2:11][O:10][C:9]1[CH:8]=[C:7]([CH:24]=[CH:23][CH:22]=1)[O:6][CH2:5][CH2:4][CH2:3][C:1]1[NH:27][N:26]=[N:25][N:2]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 145017112-[3-(3-Cyanopropoxy)phenoxymethyl]quinoline

Product 1

HCID 178420714HCID 178420714, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4.4 g of 2-[3-(3-cyanopropoxy)phenoxymethyl]quinoline, 2.6 g of sodium azide and 2.1 g of ammonium chloride in 35 ml of dry dimethylformamide was heated at 140° C. for 18 hours. The reaction mixture was poured onto ice. A solution of 20 ml of 1N sodium hydroxide was added and the solution was extracted twice with ethyl acetate. Concentrated hydrochloric acid was added to acidify the aqueous portion. This was extracted twice with ethyl acetate, dried and evaporated to give 4.5 g of a tan solid. Recrystallization from ethyl acetate gave 1.5 g of pure product of m.p. 147°-149° C.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionthe solution was extracted twice with ethyl acetate
  3. additionConcentrated hydrochloric acid was added
  4. extractionThis was extracted twice with ethyl acetate
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-8b5de536aa1742449d837c0697be0793
Source dataset
uspto-grants-1989_06
Patent number
US04839369

Reaction notes

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