Ammonia → Ethyl acetate hexane

HRID 581216

Reaction equation

HRID 581216 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.Cl.NC1C=CC(N(CC)CC)=CC=1C.[CH2:30]([OH:32])[CH3:31].N>O.[N+]([O-])([O-])=O.[Ag+]>[CH3:6][CH2:15][CH2:2][CH2:3][CH2:4][CH3:5].[C:30]([O:1][CH2:2][CH3:15])(=[O:32])[CH3:31]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 874624-HydroxyacridineHCID 108623N,N-Diethyltoluene-2,5-diamine hydrochloride

Product 1

HCID 21226206Ethyl acetate hexaneYield 19.6%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

While stirring a mixture comprising 195 mg of 4-hydroxyacridine (20), 214 mg of 2-amino-5-diethylaminotoluene hydrochloride (21) and 6.8 ml of ethanol at 20° C., a solution comprising 0.17 mg of silver nitrate dissolved in 0.75 ml of water was added thereto drop-by-drop. Next, with 0.85 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, 72.5 mg of indoaniline derivative (25) described in the exemplified compound 4-1 was obtained as deep blue crystals on recrystallization by hexane-ethyl acetate (yield 19.6%).

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, 72.5 mg of indoaniline derivative (25)

Sources & evidence

ORD record
ord-7990e67a1b6e4e92a86c9fe80ce2bee6
Source dataset
uspto-grants-1999_07
Patent number
US05919928

Linked notes

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