Sodium Hydroxide → HCID 178420714, compound

HRID 2351877Notes

Reaction equation

HRID 2351877 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, compound

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 is heated at 140° C. for 18 hours. The reaction mixture is poured onto ice. A solution of 20 ml of 1N sodium hydroxide is added and the solution is extracted twice with ethyl acetate. Concentrated hydrochloric acid is added to acidify the aqueous portion. This is extracted twice with ethyl acetate, dried and evaporated to give 4.5 g of a tan solid. Recrystallization from ethyl acetate gives 1.5 g of pure product of M.P. 147°-149° C.

Workup

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

Sources & evidence

ORD record
ord-ac4dd838556f4b9caf2d4987cda41c4a
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

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