Methyl iodide → HCID 15176763, compound

HRID 2051384Notes

Reaction equation

HRID 2051384 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:5]=1[C:6](=[O:24])[C:7]1[C:8]([Br:23])=[CH:9][CH:10]=[C:11]([NH:19][C:20](=[O:22])[CH3:21])[C:12]=1[C:13]2=[O:18])([O-:3])=[O:2].[OH-].[K+].[CH3:27]I>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC1C=CC=CC=1>[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:5]=1[C:6](=[O:24])[C:7]1[C:8]([Br:23])=[CH:9][CH:10]=[C:11]([N:19]([CH3:27])[C:20](=[O:22])[CH3:21])[C:12]=1[C:13]2=[O:18])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 19833427HCID 19833427, compound

Product 1

HCID 15176763HCID 15176763, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 5-nitro-4-bromo-1-acetylaminoanthraquinone (purity 98%, 38.7 g), monochlorobenzene (460 g), tetra-n-butyl ammonium bromide (0.3 g) and 96% potassium hydroxide (12.0 g) was stirred for 1 hour at 30° C., and then methyl iodide (28.4 g) was added at 30° C. over 2 hours. The same after-treatment as in Example 3 was conducted to obtain 5-nitro-4-bromo-N-acetyl-1-methylaminoanthraquinone (39.3 g, purity 92.3%, yield 92.3%).

Sources & evidence

ORD record
ord-16415f1a290a4ef1a108bcd5c61c6a43
Source dataset
uspto-grants-1991_05
Patent number
US05017713

Reaction notes

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