1,2-Dichlorobenzene → HCID 20507495, compound

HRID 2280047Notes

Reaction equation

HRID 2280047 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].ClC1C=CC=CC=1Cl.[Br:16][C:17]1[C:30]2[C:29](=[O:31])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22](=[O:32])[C:21]=2[C:20]([NH:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:19][CH:18]=1>CO.S(=O)(=O)(O)O>[C:1]([N:33]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[C:20]1[C:21]2[C:22](=[O:32])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29](=[O:31])[C:30]=2[C:17]([Br:16])=[CH:18][CH:19]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 7918Acetic AnhydrideHCID 150916181-Bromo-4-(cyclohexylamino)anthracene-9,10-dione

Product 1

HCID 20507495HCID 20507495, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

102 g of acetic anhydride was placed in a 20 g 1,2-dichlorobenzene solution of 76.9 g of 4-bromo1-cyclohexylaminoanthraquinone, and 1 g of concentrated sulfuric acid was placed to the solution. The solution was stirred at 110° C. for 6 hours. After the reaction was completed, the solution was diluted with 1000 g of methanol and filtered to obtain 59.8 g of 1-(acetylcyclohexylamino)-4-bromoanthraquinone (yield of 70.1%). Further, a solution of 12 g of sodium hydroxide/150 g of water was dropped to a 150 g isobutanol solution of 1-(acetylcyclohexylamino)-4-bromoanthraquinone, and the obtained solution was stirred at 90° C. for 6 hours. After the reaction was completed, the solution was cooled, the obtained solid was filtered to obtain 28.7 g of 4-bromo-1,9-N-cyclohexylanthrapyridone (70.4%). Next, 25.8 g of 2-ethylhexylamine, 8.6 g of sodium carbonate, and 6.8 g of copper powder were placed in a 40 g 1,3-dimethyl-2-imidazolidine solution of 20.4 g of 4-bromo-1,9-N-cyclohexylanthrapyridone, and the reaction was made at 190° C. for 4 hours. After the reaction was completed, the solution was cooled, diluted with ethyl acetate, and filtered. Column chromatography refining (toluene/THF) was performed to obtain 18 g of a compound (2) (yield of 82.7%). FIG. 1 illustrates a 1H NMR spectrum of the compound (2) in CDCl3 at room temperature and 400 MHz.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-0bd5753194014fea927689cd73b35172
Source dataset
uspto-grants-2015_09
Patent number
US09134639B2

Reaction notes

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