Ammonia → Ethyl acetate hexane

HRID 581214

Reaction equation

HRID 581214 reaction equation
[OH:1][C:2]1[C:15]2[C:6](=C3C(=C(F)N=2)C=CC=C3)[CH:5]=[CH:4][CH:3]=1.NC1C=CC(N(CC)CC)=C[C:19]=1[CH3:29].Cl.NC1C=CC(N(CC)CC)=CC=1C.N.[OH2:45]>[N+]([O-])([O-])=O.[Ag+].C(O)C>[CH3:6][CH2:15][CH2:2][CH2:3][CH2:4][CH3:5].[C:19]([O:1][CH2:2][CH3:15])(=[O:45])[CH3:29]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 962Water2×HCID 673642-Amino-5-(diethylamino)tolueneHCID 108623N,N-Diethyltoluene-2,5-diamine hydrochlorideHCID 541652404-Hydroxy-6-fluorophenanthridine

Product 1

HCID 21226206Ethyl acetate hexaneYield 27.1%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Procedure

While stirring a mixture comprising 59 mg of 4-hydroxy-6-fluorophenanthridine, 85 mg of 2-amino-5-diethylaminotoluene hydrochroride (21) and 4 ml of ethanol at 20° C., a solution comprising 258 mg of silver nitrate dissolved in 0.8 ml of water was added thereto drop-by-drop. Next, with 0.84 ml of 25% ammonia solution added, 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 chloroform, the extract was concentrated. After purification by column chromatography, 29 mg of indoaniline described in the exemplified compound 3-131 was obtained as deep blue crystal on recrystallization from hexane-ethyl acetate solvent (yield 27.1%).

Workup

  1. additionwas added
  2. customreaction
  3. customAfter the completion of the reaction
  4. extractionAfter extraction by chloroform
  5. concentrationthe extract was concentrated
  6. customAfter purification by column chromatography, 29 mg of indoaniline

Sources & evidence

ORD record
ord-c6246c02b4f8408d9ba68288c8c28127
Source dataset
uspto-grants-1999_07
Patent number
US05919928

Linked notes

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