Methyl iodide → HCID 15176765, compound

HRID 2051387Notes

Reaction equation

HRID 2051387 reaction equation
[Br:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[Cl:17])[C:7](=[O:18])[C:6]=2[C:5]([NH:19][C:20](=[O:22])[CH3:21])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:25]I>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC1C=CC=CC=1>[Br:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[Cl:17])[C:7](=[O:18])[C:6]=2[C:5]([N:19]([CH3:25])[C:20](=[O:22])[CH3:21])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 19833418HCID 19833418, compound

Product 1

HCID 15176765HCID 15176765, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 4-bromo-5-chloro-1-acetylaminoanthraquinone (purity 98%, 38.6 g), monochlorobenzene (460 g), tetra-n-butyl ammonium bromide (0.3 g) and 96% potassium hydroxide (12.0 g) was added methyl iodide (28.4 g) at 30° C. over 2 hours. A mixture was stirred at 30° C. for 30 minutes and 40° C. for 3 hours, successively. Then, the same after-treatment as in Example 3 was carried out to obtain 4-bromo-5-chloro-N-acetyl-1-methylaminoanthraquinone (39.3 g, purity 93.7%, yield 93.8%).

Sources & evidence

ORD record
ord-21432cc3206b4125ada01eb788ed5b44
Source dataset
uspto-grants-1991_05
Patent number
US05017713

Reaction notes

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