Sodium Hydroxide → HCID 178419994, compound

HRID 1904682Notes

Reaction equation

HRID 1904682 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:18]=[CH:17][C:16]([CH2:19][C:20]#[N:21])=[CH:15][CH:14]=1.[N-:22]=[N+:23]=[N-:24].[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:18]=[CH:17][C:16]([CH2:19][C:20]2[NH:24][N:23]=[N:22][N:21]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14501730HCID 14501730, compound

Product 1

HCID 178419994HCID 178419994, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8.6 g of 4(2-quinolylmethyloxy)phenylacetonitrile, 6.1 g of sodium azide and 5.0 g of ammonium chloride was heated with 70 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 extracted 2 times with ethyl acetate. Removal of solvent left 10.3 g of crude product. This was crystallized from methanol:ethyl acetate to yield 3.3 g of pure product of m.p. 173°-175° C.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted 2 times with ethyl acetate
  3. extractionThe aqueous fraction was extracted 2 times with ethyl acetate
  4. customRemoval of solvent
  5. waitleft 10.3 g of crude product
  6. customThis was crystallized from methanol

Sources & evidence

ORD record
ord-2b06515ff36d42118f11fc6ffc670f28
Source dataset
uspto-grants-1989_06
Patent number
US04839369

Reaction notes

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