Ethanol → N-(6'-n-octanoylhexyl)1,4-diaminoanthraquinone-2,3-dicarboximide

HRID 638525Notes

Reaction equation

HRID 638525 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:25](=[O:26])[C:24]2[C:11](=[C:12]([NH2:30])[C:13]3[C:14](=[O:29])[C:15]4[C:20]([C:21](=[O:28])[C:22]=3[C:23]=2[NH2:27])=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:9]1=[O:10].[C:31](Cl)(=[O:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[CH2:39](O)[CH3:40]>N1C=CC=CC=1>[C:31]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:25](=[O:26])[C:24]2[C:11](=[C:12]([NH2:30])[C:13]3[C:14](=[O:29])[C:15]4[C:20]([C:21](=[O:28])[C:22]=3[C:23]=2[NH2:27])=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:9]1=[O:10])(=[O:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:39][CH3:40]

Participants

5

Reactant 3

HCID 702EthanolHCID 67340Hexanoyl chlorideHCID 86740572N-(6'-hydroxyhexyl)1,4-diaminoanthraquinone-2,3-dicarboximide

Product 1

HCID 86740573N-(6'-n-octanoylhexyl)1,4-diaminoanthraquinone-2,3-dicarboximideYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of N-(6'-hydroxyhexyl)1,4-diaminoanthraquinone-2,3-dicarboximide (10.0 parts) in pyridine (200.0 parts) was heated to 90° C. under nitrogen and maintained at this temperature for 1 hour or until complete dissolution of the dye. The reaction mixture was cooled to 40° C. Caproyl chloride (6.9 parts) was then added dropwise at a rate such that the temperature did not exceed 50° C. The reaction mixture was cooled to room temperature. After 3 hours, ethanol (20.0 parts) was added dropwise. The mixture was cooled in ice for 3 hours. The dark blue solid obtained was separated by filtration and washed with methanol (100 parts). After drying in high vacuo for 6 hours at 45° C., there was obtained N-(6'-n-octanoylhexyl)1,4-diaminoanthraquinone-2,3-dicarboximide (11.5 parts, 88% from N-(6'-hydroxyhexyl)1,4-diaminoanthraquinone-2,3-dicarboximide) (Formula 6); m.p.: 157°-158° C.; lambdamax 680 nm.

Workup

  1. temperaturemaintained at this temperature for 1 hour or until complete dissolution of the dye
  2. temperatureThe reaction mixture was cooled to 40° C
  3. customdid not exceed 50° C
  4. temperatureThe reaction mixture was cooled to room temperature
  5. temperatureThe mixture was cooled in ice for 3 hours
  6. customThe dark blue solid obtained
  7. customwas separated by filtration
  8. washwashed with methanol (100 parts)
  9. customAfter drying in high vacuo for 6 hours at 45° C.

Sources & evidence

ORD record
ord-b9cfebf9b35a4eb488c6f518c7022dbd
Source dataset
uspto-grants-1985_12
Patent number
US04562135

Reaction notes

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