Sulfuric Acid → HCID 20507495, compound

HRID 1422418Notes

Reaction equation

HRID 1422418 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Br:8][C:9]1[C:22]2[C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:24])[C:13]=2[C:12]([NH:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:11][CH:10]=1.S(=O)(=O)(O)O>ClC1C=CC=CC=1Cl.CO>[C:1]([N:25]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:12]1[C:13]2[C:14](=[O:24])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21](=[O:23])[C:22]=2[C:9]([Br:8])=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 150916181-Bromo-4-(cyclohexylamino)anthracene-9,10-dione

Product 1

HCID 20507495HCID 20507495, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
110 °C

Procedure

102 Grams of acetic anhydride were loaded into a solution of 76.9 g of 4-bromo-1-cyclohexylaminoanthraquinone in 20 g of 1,2-dichlorobenzene and then 1 g of concentrated sulfuric acid was charged into the mixture, followed by stirring at 110° C. for 6 hours. After the completion of the reaction, the reaction product was diluted with 1,000 g of methanol and filtered. Thus, 59.8 g of 1-(acetylcyclohexylamino)-4-bromoanthraquinone were obtained (70.1% yield). Further, a solution of 12 g of caustic soda in 150 g of water was dropped to a solution of 1-(acetylcyclohexylamino)-4-bromoanthraquinone in 150 g of isobutanol and then the mixture was stirred at 90° C. for 6 hours. After the completion of the reaction, the reaction product was cooled and then the resultant solid was separated by filtration. Thus, 28.7 g of 4-bromo-1,9-N-cyclohexylanthrapyridone were obtained (70.4% yield). Next, 19.3 g of 4-methylanilinehexylamine, 8.6 g of sodium carbonate, and 6.8 g of copper powder were loaded into a solution of 20.4 g of 4-bromo-1,9-N-cyclohexylanthrapyridone in 40 g of 1,3-dimethyl-2-imidazolidine, and then the mixture was subjected to a reaction at 190° C. for 4 hours. After the completion of the reaction, the reaction product was cooled, diluted with ethyl acetate, and filtered. The filtrate was purified by column chromatography (toluene/THF). Thus, 17.6 g of a compound (16) were obtained (85.0% yield). FIG. 1 illustrates the 1H-NMR spectrum of the compound (16) in CDCl3 at room temperature and 400 MHz.

Workup

  1. customAfter the completion of the reaction
  2. filtrationfiltered

Sources & evidence

ORD record
ord-54f45ea10d0c47928b95467234a64d88
Source dataset
uspto-grants-2015_01
Patent number
US08926740B2

Reaction notes

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