N-Methylethylenediamine → 9,10-Anthracenedione, 1,4-bis((2-(methylamino)ethyl)amino)- (9CI)

HRID 1719472Notes

Reaction equation

HRID 1719472 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([OH:18])=[C:8]3[C:13](=[C:14]([OH:15])[C:4]2=[CH:3][CH:2]=1)[C:12](O)=[CH:11][CH:10]=[C:9]3O.[CH3:19][NH:20][CH2:21][CH2:22][NH2:23]>>[CH3:19][NH:20][CH2:21][CH2:22][NH:23][C:12]1[C:13]2[C:14](=[O:15])[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:7](=[O:18])[C:8]=2[C:9]([NH:23][CH2:22][CH2:21][NH:20][CH3:19])=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 8014N-MethylethylenediamineHCID 680631,4,9,10-Anthracenetetrol

Product 1

HCID 1003719,10-Anthracenedione, 1,4-bis((2-(methylamino)ethyl)amino)- (9CI)

Conditions

Temperature
50 °C

Procedure

A mixture of 2.4 g. of leuco-quinizarin and 25 g. of de-aerated N-methylethylenediamine is heated at 50° C. with stirring under nitrogen for one hour. Heating at 50° C. is continued as air is bubbled into the mixture for 40 minutes. The mixture is evaporated to dryness, then re-evaporated twice from 25 ml. portions of ethanol. Crystallization of the residue from ethanol-ether at -70° C. gives 2.32 g. of crude solid which is recrystallized twice from carbon tetrachloride giving 1.92 g. of the desired product as dark blue crystals, mp. 131°-132° C.

Workup

  1. additionA mixture of 2.4 g
  2. customis bubbled into the mixture for 40 minutes
  3. customThe mixture is evaporated to dryness
  4. customre-evaporated twice from 25 ml
  5. customCrystallization of the residue from ethanol-ether at -70° C.
  6. customgives 2.32 g
  7. customof crude solid which is recrystallized twice from carbon tetrachloride giving 1.92 g

Sources & evidence

ORD record
ord-7563c4c87efa48c3a36f10003711a635
Source dataset
uspto-grants-1985_09
Patent number
US04540583

Reaction notes

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