Ammonium Chloride → HCID 178479868, compound

HRID 2083204Notes

Reaction equation

HRID 2083204 reaction equation
[CH3:1][N:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5](=[O:12])[C:4]2[CH:13]=[C:14]([C:17]#[N:18])[CH:15]=[CH:16][C:3]1=2.[Cl-].[NH4+].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O>[CH3:1][N:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5](=[O:12])[C:4]2[CH:13]=[C:14]([C:17]3[NH:23][N:22]=[N:21][N:18]=3)[CH:15]=[CH:16][C:3]1=2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 20358126HCID 20358126, compound

Product 1

HCID 178479868HCID 178479868, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5 g of 10-methyl-5-oxo-5H,10H-benzo[b][1,8]naphthyridine-7-carbonitrile, 50 ml of dimethylformamide, 1.45 g of ammonium chloride and 1.8 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 4.3 g of 10-methyl-7-(5-1H-tetrazolyl)-5-oxo-5H,10H-benzo[b][1,8]naphthyridine melting at 321° C with decomposition.

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-80f92021826d4da384305e186d972505
Source dataset
uspto-grants-1978_04
Patent number
US04085111

Reaction notes

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