Potassium Carbonate → HCID 87708343, compound

HRID 2081234Notes

Reaction equation

HRID 2081234 reaction equation
BrC1C2[C:14](=O)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=O)C=2C(NC)=CC=1.Cl[C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[NH:24][C:25](=O)[CH3:26].[C:31](=O)([O-])[O-:32].[K+].[K+]>ClC1C=CC=CC=1Cl.[Cu]>[C:31]1(=[O:32])[C:22]2[C:21]3[C:30]([CH:29]=[CH:28][C:23]=2[N:24]=[CH:25][CH2:26]1)=[CH:7][C:8]1[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:14]=3

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 114933-ChloroacetanilideHCID 314189,10-Anthracenedione, 1-bromo-4-(methylamino)-

Product 1

HCID 87708343HCID 87708343, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 1-bromo-4-methylaminoanthraquinone (16 parts) of the following formula: ##STR10## and m-chloroacetoanilide (12.7 parts) of the following formula: ##STR11## was heated at 135°-145° C. for 25 hours in o-dichlorobenzene in the presence of metallic copper (powder, 0.3 part) and potassium carbonate (17.3 parts). After cooling, the resulting precipitate was filtrated, washed with methanol and then water and dried to obtain a cake (13.5 parts, yield 70%) of anthrapyridone compound of the following formula: This compound showed a single red spot when thin-layer-chromatographed and λ max (in N,N-dimethylformamide) of 547 nm and had a melting point of 281°-284° C. (uncorrected).

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was filtrated
  3. washwashed with methanol
  4. dry with materialwater and dried

Sources & evidence

ORD record
ord-8e94638384fc42adb246178309dd90bc
Source dataset
uspto-grants-1993_02
Patent number
US05183892

Reaction notes

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