Methyl iodide → 4-bromo-N-benzoyl-1-methylaminoanthraquinone

HRID 2051386Notes

Reaction equation

HRID 2051386 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][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([NH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[OH-].[K+].[CH3:29]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][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([N:18]([CH3:29])[C:19](=[O:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 66478Benzamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-

Product 1

HCID 197994454-bromo-N-benzoyl-1-methylaminoanthraquinoneYield 98.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 4-bromo-1-benzoylaminoanthraquinone (purity 98.5%, 41.2 g), monochlorobenzene (500 g), tetra-n-butyl ammonium bromide (0.3 g) and 96% potassium hydroxide (12.0 g) was stirred for one hour at 30° C., and methyl iodide (28.4 g) was added thereto 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 aftertreatment as in Example 3 was conducted to obtain 4-bromo-N-benzoyl-1-methylaminoanthraquinone (41.8 g, purity 94.5%, yield 94.0%).

Workup

  1. waitat 30° C. over 2 hours
  2. stirringA mixture was stirred at 30° C. for 30 minutes and 40° C. for 3 hours

Sources & evidence

ORD record
ord-d62b05b76a314df29a8b02d68b0fca29
Source dataset
uspto-grants-1991_05
Patent number
US05017713

Reaction notes

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