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Ethylene Glycol → Ethyl acetate hexane

HRID 581215
Notes
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Reaction equation

HRID 581215 reaction equation
Cl.[CH:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([C:14]=2NNS(C2C=C[C:24]([CH3:27])=CC=2)(=O)=O)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1.[OH-:28].[Na+].[CH2:30]([OH:33])[CH2:31][OH:32]>O>[CH3:31][O:32][C:5]1[C:6]2[C:15](=[CH:14][C:13]3[C:8]([N:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:2]=[CH:3][CH:4]=1.[CH3:14][CH2:15][CH2:2][CH2:3][CH2:4][CH3:5].[C:30]([O:33][CH2:24][CH3:27])(=[O:28])[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 86753010N1-9-acridinyl-N2-p-toluenesulfonylhydrazine hydrochloride

Product 2

HCID 122924034-MethoxyacridineHCID 21226206Ethyl acetate hexaneYield 95.2%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixed solution comprising 124 mg of N1 -9-(4-methoxy)acridinyl-N2 -p-toluenesulfonylhydrazine hydrochloride (18), 40 mg of sodium hydroxide, and 5 ml of ethylene glycol was allowed to react at 100° C. for a period of one hour. After the completion of the reaction, the reacted solution was introduced into water and the product was extracted by ethyl acetate. After ethyl acetate was distilled away, the residue was purified by column chromatography and 57.6 mg of 4-methoxyacridine (19) was obtained as crystals on recrystallization by hexane-ethyl acetate (yield 95.2%).

Workup

  1. customto react at 100° C. for a period of one hour
  2. customAfter the completion of the reaction
  3. extractionthe product was extracted by ethyl acetate
  4. distillationAfter ethyl acetate was distilled away
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5540965854974b8dac9651972b41a0c4
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05919928

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes