Hydrochloric Acid → HCID 20574102, compound

HRID 895073Notes

Reaction equation

HRID 895073 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[NH:14][N:13]=[N:12][N:11]=1.[N:15]([O-])=O.[Na+].Cl>C(Cl)(Cl)Cl>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]2[C:10]3[N:11]([N:12]=[N:13][N:14]=3)[N:15]=[N:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 178489171HCID 178489171, compound

Product 1

HCID 20574102HCID 20574102, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The above-named compound was prepared from 1 g of 5-(2-amino-4-methoxyphenyl)tetrazole, 0.45 g of NaNO2, and concentrated HCl and isolated from the reaction mixture by the procedures of Example 2. The residue obtained by evaporation of the chloroform extracts was a dark reddish-brown solid shown by liquid chromatographic analysis to be largely the named compound plus several minor impurities. The product was purified by percolating its chloroform solution through two 7-10 ml portions of 80-200 mesh alumina and evaporating the treated solution under nitrogen at room temperature. A yield of 0.54 g of orange solid was obtained. This purified material showed only trace impurities on thin layer chromatographic examination and its structure as the named compound was confirmed by magnetic resonance and infrared absorption analyses.

Workup

  1. customisolated from the reaction mixture by the procedures of Example 2
  2. customThe product was purified
  3. customevaporating the treated solution under nitrogen at room temperature

Sources & evidence

ORD record
ord-dd4a3ee98a4545a4b096d2f169554d9b
Source dataset
uspto-grants-1981_08
Patent number
US04286090

Reaction notes

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