9,10-Anthracenedicarboxaldehyde → HCID 74054432, compound

HRID 128070

Reaction equation

HRID 128070 reaction equation
[CH:1]1[C:14]2[C:5](=[C:6]([CH:17]=O)[C:7]3[C:12]([C:13]=2[CH:15]=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][NH:23][NH2:24]>C(O)(=O)C.C(O)C>[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][NH:23][N:24]=[CH:15][C:13]1[C:14]2[C:5]([C:6]([CH:17]=[N:24][NH:23][CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])=[C:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)=[CH:4][CH:3]=[CH:2][CH:1]=2

Participants

5

Reactant 2

HCID 815009,10-AnthracenedicarboxaldehydeHCID 1205522-Hydrazinyl-N,N-dimethylethanamine

Product 1

HCID 74054432HCID 74054432, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A suspension of 4.68 g. of anthracene-9,10-dicarboxaldehyde in 100 ml. of ethanol containing 4.13 g. of [2-(dimethylamino)ethyl]hydrazine [Elslager et al., J. Med. Chem. I, 493 (1964)] containing two drops of acetic acid is stirred and heated under reflux for two hours. The resulting solution is filtered, concentrated, allowed to cool to 45° C., diluted with petroleum ether, then allowed to cool further at 5° C. The desired product separates as an orange solid and is collected by filtration.

Workup

  1. additionA suspension of 4.68 g
  2. temperatureheated
  3. temperatureunder reflux for two hours
  4. filtrationThe resulting solution is filtered
  5. concentrationconcentrated
  6. additiondiluted with petroleum ether
  7. temperatureto cool further at 5° C
  8. filtrationis collected by filtration

Sources & evidence

ORD record
ord-7b4b9529bc7c400dba32d8fc1bff9d82
Source dataset
uspto-grants-1981_03
Patent number
US04258181

Linked notes

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