Hydrochloric Acid → HCID 13423346, compound

HRID 1248580Notes

Reaction equation

HRID 1248580 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]1[O:6][C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH3:15])=[CH:11][CH:10]=[CH:9][C:8]=2[C:17](Cl)=[O:18].[CH2:23]([N:25]([CH2:29][CH3:30])[CH2:26][CH2:27][NH2:28])[CH3:24].Cl>C1C=CC=CC=1>[CH2:23]([N:25]([CH2:29][CH3:30])[CH2:26][CH2:27][NH:28][C:17]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[O:6][C:5]([C:4]1[CH:20]=[CH:21][CH:22]=[C:2]([Cl:1])[CH:3]=1)=[C:14]([CH3:15])[C:13]2=[O:16])=[O:18])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 60993N,N-DiethylethylenediamineHCID 54253261HCID 54253261, compound

Product 1

HCID 13423346HCID 13423346, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3'-chloro-3-methylflavone-8-carboxylic acid chloride (prepared from 1.00 g of 3'-chloro-3-methylflavone-8-carboxylic acid and 0.46 ml of thionyl chloride) in 40 ml of benzene were added 0.33 g of N,N-diethylethylenediamine and the solution was stirred for 80 minutes at room temperature. To the reaction mixture was added aqueous HCl solution and shaken. The water layer was separated and made alkaline with potassium carbonate and extracted with chloroform. The extract was washed with water, dried, and evaporated. The residue was purified by column chromatography (adsorbent: silica gel, eluted with chloroform and chloroform containing 1% of methanol) to give 0.39 g of yellow crystals, which were recrystallized from isopropyl ether as colorless plates, m.p. 116°-117° C.

Workup

  1. stirringshaken
  2. customThe water layer was separated
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was purified by column chromatography (adsorbent: silica gel, eluted with chloroform and chloroform containing 1% of methanol)

Sources & evidence

ORD record
ord-4d65274feb8646c781713ba2b306f68c
Source dataset
uspto-grants-1985_06
Patent number
US04525356

Reaction notes

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