Acetic Acid → 1,8-Bis(p-n-butylbenzylidene amino)anthraquinone

HRID 262414Notes

Reaction equation

HRID 262414 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[NH2:17])[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:19]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22].[C:31](O)(=O)[CH3:32]>CO>[CH2:19]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[N:1][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][C:12]=4[N:17]=[CH:12][C:13]4[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][CH2:31][CH3:32])=[CH:15][CH:14]=4)[C:7](=[O:18])[C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 85111,8-Diamino-9,10-anthracenedioneHCID 709884-Butylbenzaldehyde

Product 1

HCID 201633541,8-Bis(p-n-butylbenzylidene amino)anthraquinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution at 80° C. of 2.38g (0.1 mol) 1,8-diaminoanthraquinone in 3.16 g (0.2 mol) p-n-butylbenzaldehyde is added about 1 ml. glacial acetic acid. Heating is continued for one hour and 50 ml methanol is added to dissolve the reaction mixture. The solution is poured into 100 ml ice water and the product collected and recrystallized from 1:1 methanol-water as above to give 1,8-bis(p-n-butylbenzylidene amino)anthraquinone as fine purple needles, melting with decomposition at 288°-9° C.

Workup

  1. temperatureHeating
  2. dissolutionto dissolve the reaction mixture
  3. customthe product collected
  4. customrecrystallized from 1:1 methanol-water as above

Sources & evidence

ORD record
ord-94babcba62ad429cbb12b7eaea0d102d
Source dataset
uspto-grants-1979_05
Patent number
US04154746

Reaction notes

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