Pyridine → 10-Propionyl dithranol

HRID 2309744Notes

Reaction equation

HRID 2309744 reaction equation
[CH:1]1[CH:2]=[C:3]2[CH2:17][C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:10]=3[C:8](=[O:9])[C:4]2=[C:5]([OH:7])[CH:6]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>C1(C)C=CC=CC=1>[OH:16][C:15]1[C:10]2[C:8](=[O:9])[C:4]3[C:3](=[CH:2][CH:1]=[CH:6][C:5]=3[OH:7])[CH:17]([C:24](=[O:27])[CH2:25][CH3:26])[C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 2202AnthralinHCID 62324Propionyl chloride2×

Product 1

HCID 12652210-Propionyl dithranol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 56.6 g (0.25 mol) of purified anthralin in 1750 m3 of anhydrous toluene at room temperature, 27.3 cm3 (0.34 mol) of anhydrous pyridine was added first and then 26.2 cm3 (0.3 mol) of propionyl chloride was added dropwise in around 20 minutes. The mixture was then heated to around 85° C. for 1 hour. The mixture was recooled to room temperature, 27.3 cm3 of pyridine and 26.2 cm3 of propionyl chloride were again added and the mixture was heated for 1 hour to a temperature of around 85° C.

Workup

  1. customwas recooled to room temperature
  2. temperaturethe mixture was heated for 1 hour to a temperature of around 85° C.

Sources & evidence

ORD record
ord-0a50b59f8be04da7b9b8a6265b1bb222
Source dataset
uspto-grants-1987_09
Patent number
US04696941

Reaction notes

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