Dimethylformamide → HCID 178419997, compound

HRID 1904680Notes

Reaction equation

HRID 1904680 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][C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])=[CH:15][CH:14]=1.[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].[NH4+].CN(C)C=O>[OH-].[Na+]>[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][C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21]2[NH:27][N:26]=[N:25][N:22]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14501727HCID 14501727, compound

Product 1

HCID 178419997HCID 178419997, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 8.0 g of 4-[4-(2-quinolylmethyloxy)phenoxy]butyronitrile, 4.9 g of sodium azide and 4.0 g of ammonium chloride was heated with 25 ml of dry dimethylformamide at 140° C. for 20 hours. The reaction mixture was poured into ice, basified in 1N sodium hydroxide and extracted 2 times with warm ethyl acetate. The aqueous fraction was acidified with acetic acid. The product was filtered and washed with water to give 6.6 g of crude product. Crystallization from ethyl acetate gave 4.2 g of the light tan product, m.p. 158°-160° C.

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted 2 times with warm ethyl acetate
  3. filtrationThe product was filtered
  4. washwashed with water
  5. customto give 6.6 g of crude product
  6. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-1f1ea49786514d5fbc30196b65186096
Source dataset
uspto-grants-1989_06
Patent number
US04839369

Reaction notes

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