Ammonia → Ethyl acetate hexane

HRID 482153

Reaction equation

HRID 482153 reaction equation
[OH:1][C:2]1[C:15]2[C:6](=C3C(=CN=2)C=CC=C3)[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 108623N,N-Diethyltoluene-2,5-diamine hydrochlorideHCID 22625105Phenanthridin-4-ol

Product 1

HCID 21226206Ethyl acetate hexaneYield 35.1%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

A mixture comprising 390 mg of 4-hydroxyphenanthridine (13), 430 mg of 2-amino-5-diethylaminotoluene hydrochloride (21) and 15 ml of ethanol was stirred at 20° C. and a solution comprising 1.02 g of silver nitrate dissolved in 4.5 ml of water was added thereto drop-by-drop. Then, 1.7 ml of 25% ammonia solution was added and the 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, 259 mg of deep blue crystal of indoaniline (22) was obtained on recrystallization by hexane-ethyl acetate (yield 35.1%).

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, 259 mg of deep blue crystal of indoaniline (22)

Sources & evidence

ORD record
ord-d64100bd7a7443fc8b02c3cf82910eff
Source dataset
uspto-grants-1998_08
Patent number
US05792863

Linked notes

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