Dimethylformamide → HCID 178422583, compound

HRID 1995326Notes

Reaction equation

HRID 1995326 reaction equation
[C:1]([C:3]1[C:14]2=[C:15]3[N:10]([CH:11]([CH3:16])[CH2:12][CH2:13]2)[CH:9]=[C:8]([C:17]([OH:19])=[O:18])[C:7](=[O:20])[C:6]3=[CH:5][CH:4]=1)#[N:2].[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+].CN(C)C=O>C(O)(=O)C.O>[CH3:16][CH:11]1[N:10]2[C:15]3[C:6](=[CH:5][CH:4]=[C:3]([C:1]4[NH:23][N:22]=[N:21][N:2]=4)[C:14]=3[CH2:13][CH2:12]1)[C:7](=[O:20])[C:8]([C:17]([OH:19])=[O:18])=[CH:9]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13156220HCID 13156220, compound

Product 1

HCID 178422583HCID 178422583, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1.4 g (5 mmole) of 8-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 0.75 g (11 mmole) of sodium azide, 0.6 g (11 mmole) of ammonium chloride and 50 ml of N,N-dimethylformamide was heated at 120° C. for three days in a sealed vessel followed by decantation into 100 ml of water. To this mixture was added 2 ml of glacial acetic acid, and the mixture was cooled. The solid was separated by filtration and recrystallized from aqueous N,N-dimethylformamide to provide white needles of 6,7-dihydro-5-methyl-1-oxo-8-(5-tetrazolyl)-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, m.p. 270° C. (dec.). Analysis: Calculated for C15H13N5O3 : %C, 57.9; %H, 4.2; %N, 22.5; Found: %C 57.8; %H, 4.0; %N, 22.7. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. temperaturethe mixture was cooled
  2. customThe solid was separated by filtration
  3. customrecrystallized from aqueous N,N-dimethylformamide

Sources & evidence

ORD record
ord-0677afbdaad94cf9b333602dfad7d75f
Source dataset
uspto-grants-1983_09
Patent number
US04404207

Reaction notes

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