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Ammonia → Ethyl acetate hexane

HRID 482159
Notes
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Reaction equation

HRID 482159 reaction equation
[OH:1][C:2]1[C:15]2[C:6](=CC3C(N=2)=CC=CC=3)[CH:5]=[CH:4][CH:3]=1.C(C(CCCC)CN(CC(CC)CCCC)C1C=CC(N)=CC=1)C.[CH2:40]([OH:42])[CH3:41].N>O.[N+]([O-])([O-])=O.[Ag+]>[CH3:6][CH2:15][CH2:2][CH2:3][CH2:4][CH3:5].[C:40]([O:1][CH2:2][CH3:15])(=[O:42])[CH3:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 874624-HydroxyacridineHCID 53999179n,n-Di(2-ethylhexyl)-p-phenylenediamine

Product 1

HCID 21226206Ethyl acetate hexaneYield 12.9%

Reagents, catalysts & solvents 2

HCID 24470
Silver Nitrate
Catalyst
HCID 962WaterSolvent2×

Procedure

While stirring a mixture comprising 2.87 g of 4-hydroxyacridine (20), 4.89g of N,N-di(2-ethylhexyl)-p-phenylenediamine and 100 ml of ethanol at 20° C., a solution comprising 7.48 g of silver nitrate dissolved in 33.1 ml of water was added thereto drop-by-drop. Next, with 12.5 ml of 25% ammonia solution added to the mixture, reaction was allowed to proceed at 20° C. for a period of 24 hr. After the completion of the reaction, the reacted solution was introduced into water. After extraction by ethyl acetate, the extract was concentrated. After purification by column chromatography, 0.99 g of indoaniline described in the exemplified compound 4-10 was obtained as deep blue crystals on recrystallization by hexane-ethyl acetate (yield 12.9%).

Workup

  1. additionwas added
  2. customAfter the completion of the reaction
  3. extractionAfter extraction by ethyl acetate
  4. concentrationthe extract was concentrated
  5. customAfter purification by column chromatography, 0.99 g of indoaniline

Sources & evidence

ORD record
ord-a4942f298a5140c38baf301e1913712b
Source dataset
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05792863

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes