Isoamyl Nitrite → 7-Chloro-2-methyl-3-nitrosoimidazo[2,1-a]isoquinoline

HRID 1788930Notes

Reaction equation

HRID 1788930 reaction equation
[N:1](OCCC(C)C)=[O:2].[Cl:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][N:14]1[CH:22]=[C:21]([CH3:23])[N:20]=[C:15]12>O1CCOCC1>[Cl:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][N:14]1[C:22]([N:1]=[O:2])=[C:21]([CH3:23])[N:20]=[C:15]12

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 138218267-Chloro-2-methylimidazo[2,1-a]isoquinoline

Product 1

HCID 138218497-Chloro-2-methyl-3-nitrosoimidazo[2,1-a]isoquinolineYield 39.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Isoamyl nitrite (140 g) was added to a suspension of 7-chloro-2-methylimidazo[2,1-a]isoquinoline (17.1 g) in dioxane (170 ml) at 50° C. and the mixture was refluxed for 15 minutes. After being cooled, the resulting precipitate was collected by filtration, washed successively with dioxane and diethyl ether and dried in a desiccator to give 7-chloro-2-methyl-3-nitrosoimidazo[2,1-a]isoquinoline (7.7 g).

Workup

  1. temperaturethe mixture was refluxed for 15 minutes
  2. temperatureAfter being cooled
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed successively with dioxane and diethyl ether
  5. customdried in a desiccator

Sources & evidence

ORD record
ord-bad33391a14d457ea99c0d986f93938b
Source dataset
uspto-grants-1987_08
Patent number
US04686227

Reaction notes

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