Dimethylamine → 7-Chloro-3-dimethylaminomethyl-2-methylimidazo[2,1-a]isoquinoline

HRID 649147Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 37% aqueous formaldehyde (0.42 g) and 50% aqueous dimethylamine (0.46 g) in acetic acid (3.2 ml) was added 7-chloro-2-methylimidazo[2,1-a]isoquinoline (1 g) and the mixture was warmed at 50° C. with stirring for 3.5 hours. The solution was poured into ice water and neutralized with an aqueous solution of sodium hydroxide. The resulting precipitates were collected by filtration, washed with water and recrystallized from a mixture of toluene and n-hexane to give 7-chloro-3-dimethylaminomethyl-2-methylimidazo[2,1-a]isoquinoline (0.9 g).

Workup

customThe resulting precipitates
filtrationwere collected by filtration
washwashed with water
customrecrystallized from a mixture of toluene and n-hexane

Sources & evidence

ORD record: ord-99d78b8f117249fcb3a423514fbefa4b
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04738967

Reaction notes

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