Iodoethane → 7-Chloro-3-diethylamino-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline

HRID 376325Notes

Reaction equation

HRID 376325 reaction equation
[NH2:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]3[C:14]([C:5]2=[N:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:15].[CH2:23](I)[CH3:24].N[C:27]1N2C=CC3C(C2=N[C:28]=1C1C=CC=CC=1C)=CC=CC=3.[CH2:47](Br)[CH:48]=C>>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[CH:7][N:6]1[C:2]([NH:1][CH2:23][CH3:24])=[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])[N:4]=[C:5]12.[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[CH:7][N:6]1[C:2]([N:1]([CH2:47][CH3:48])[CH2:27][CH3:28])=[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])[N:4]=[C:5]12

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 7841Allyl bromideHCID 15462240HCID 15462240, compoundHCID 186911833-Amino-7-chloro-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline2×

Product 2

HCID 154625757-Chloro-3-diethylamino-2-(2-methylphenyl)imidazo[2,1-a]isoquinolineHCID 186911527-Chloro-3-ethylamino-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline

Procedure

Example 10 was repeated except that 3-amino-7-chloro-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline (Compound 5) and ethyl iodide were used in place of 3-amino-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline and allyl bromide, which gave 7-chloro-3-ethylamino-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline (Compound 159) as yellow needles and 7-chloro-3-diethylamino-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline (Compound 199) as colorless needles.

Sources & evidence

ORD record
ord-06a647aba0e04f20b2b495becc18e101
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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