Hydrochloric Acid → HCID 178432027, compound

HRID 1788928Notes

Reaction equation

HRID 1788928 reaction equation
[C:1]([CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][C:11]3[C:16]([C:7]2=[N:6][C:5]=1[CH3:17])=[CH:15][CH:14]=[CH:13][CH:12]=3)#[N:2].[Cl-].[NH4+].[N-:20]=[N+:21]=[N-:22].[Na+].Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[CH3:17][C:5]1[N:6]=[C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][N:8]2[C:4]=1[CH2:3][C:1]1[NH:22][N:21]=[N:20][N:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 13821835HCID 13821835, compound

Product 1

HCID 178432027HCID 178432027, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-cyanomethyl-2-methylimidazo[2,1-a]isoquinoline (2.8 g), ammonium chloride (0.74 g) and sodium azide (0.9 g) in N,N-dimethylformamide (28 ml) was heated at 120°-125° C. with stirring for 18 hours. The solution was poured into water, acidified with concentrated hydrochloric acid and then neutralized with an aqueous solution of sodium bicarbonate. The resulting precipitates were collected by filtration, washed with water and recrystallized from a mixture of chloroform and methanol to give 2-methyl-3-[(1H- tetrazol-5-yl)methyl]imidazo[2,1-a]isoquinoline (2.9 g).

Workup

  1. temperaturewas heated at 120°-125° C.
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customrecrystallized from a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-9ea9b772f2ac449680941eb9538ee16f
Source dataset
uspto-grants-1987_08
Patent number
US04686227

Reaction notes

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