Hydrochloric Acid → HCID 178518586, compound

HRID 648446Notes

Reaction equation

HRID 648446 reaction equation
[C:1]([C:3]1[C:4](=[O:13])[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].[Cl-].[NH4+].[N-:16]=[N+:17]=[N-:18].[Na+].Cl>CN(C)C=O.O>[NH:16]1[C:1]([C:3]2[C:4](=[O:13])[NH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[N:2][N:18]=[N:17]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 27645772-Oxo-1,2-dihydroquinoline-3-carbonitrile

Product 1

HCID 178518586HCID 178518586, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5.0 g of 3-cyano-2(1H)-quinolinone, 1.9 g of ammonium chloride and 2.4 g of sodium azide in 50 ml of dimethylformamide was heated at 120° C for 16 hours. The mixture was then poured into 250 ml of water and the resulting mixture was acidified to pH 2 with concentrated hydrochloric acid. The solid which formed was separated by filtration and dried. It was then dissolved in aqueous sodium hydroxide and the aqueous solution was washed with methylene chloride and filtered and the filtrate was acidified with hydrochloric acid. The light tan solid which formed was separated by filtration and dried to give 3-(IH-tetrazol-5-yl)-2(1H)-quinolinone 1/9 hydrate melting at about 301°-303° C. with decomposition.

Workup

  1. customThe solid which formed
  2. customwas separated by filtration
  3. customdried
  4. dissolutionIt was then dissolved in aqueous sodium hydroxide
  5. washthe aqueous solution was washed with methylene chloride
  6. filtrationfiltered
  7. customThe light tan solid which formed
  8. customwas separated by filtration
  9. customdried

Sources & evidence

ORD record
ord-c35b2ec722ac485e90d15c845af610de
Source dataset
uspto-grants-1988_04
Patent number
US04735948

Reaction notes

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