Ammonium Chloride → HCID 178514904, compound

HRID 2083202Notes

Reaction equation

HRID 2083202 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4]2[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][C:3]1=2.[Cl-].[NH4+].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[NH:20]1[C:16]([C:14]2[CH:13]=[CH:12][C:4]3[O:5][C:6]4=[N:7][CH:8]=[CH:9][CH:10]=[C:11]4[C:2](=[O:1])[C:3]=3[CH:15]=2)=[N:17][N:22]=[N:21]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 128984545-Oxo-5H-[1]benzopyrano[2,3-b]pyridine-7-carbonitrile

Product 1

HCID 178514904HCID 178514904, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 34 g of 5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-7-carbonitrile, 460 ml of dimethylformamide, 10.5 g of ammonium chloride and 13.1 g of sodium azide is heated with stirring at 110° C to 120° C for 20 hours. After cooling, crystals are filtered off and added to a dilute hydrochloric acid, and the mixture is stirred. The crystals are filtered off, washed with water and recrystallized from dimethylformamide to give 29 g of 7-(5-1H-tetrazolyl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine melting at above 300° C.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling
  3. filtrationcrystals are filtered off
  4. additionadded to a dilute hydrochloric acid
  5. stirringthe mixture is stirred
  6. filtrationThe crystals are filtered off
  7. washwashed with water
  8. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-a5ad2deddd744ec988fec33b309def66
Source dataset
uspto-grants-1978_04
Patent number
US04085111

Reaction notes

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