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

HRID 1788922Notes

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-181a7e40fb93472d9d081e58c92d33b5
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04686227

Reaction notes

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