Diethyl Ether → Acridine-9-carbonyl chloride hydrochloride

HRID 2256800Notes

Reaction equation

HRID 2256800 reaction equation
O.[CH:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([C:14]=2[C:16]([OH:18])=O)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1.C(OCC)C.S(Cl)([Cl:26])=O>>[ClH:26].[CH:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([C:14]=2[C:16]([Cl:26])=[O:18])=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 162116879-Acridinecarboxylic Acid Hydrate

Product 1

HCID 12395930Acridine-9-carbonyl chloride hydrochlorideYield 100%

Conditions

Temperature
100 °C

Procedure

A mixture of 9-acridinecarboxylic acid hydrate (10.0 g, 44.80 mmol) in 80 mL of thionyl chloride was refluxed at 100° C. under nitrogen for 2 hours, and then cooled to 25° C. The resulting solution was reduced to about half the original volume under reduced pressure, and then poured into 500 mL of anhydrous diethyl ether. The yellow precipitate was collected, washed with ether (3×100 mL), and dried under reduced pressure for 2 hours, to produce 12.95 g (~ 100% yield) of the product, which was used immediately for the next reaction.

Workup

  1. temperaturecooled to 25° C
  2. customThe yellow precipitate was collected
  3. washwashed with ether (3×100 mL)
  4. customdried under reduced pressure for 2 hours

Sources & evidence

ORD record
ord-b93f61a3cba441c89a839d80d6415607
Source dataset
uspto-grants-1997_08
Patent number
US05656426

Reaction notes

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