Water → 5,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 1082044Notes

Reaction equation

HRID 1082044 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].N1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2N)[CH2:8][CH2:7][CH2:6]1.O>CCOCC>[NH:1]1[C:13]2=[C:14]3[C:9](=[CH:10][CH:11]=[CH:12]2)[CH2:8][CH2:7][CH2:6][N:4]3[C:2]1=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 1176UreaHCID 1046728-Quinolinamine, 1,2,3,4-tetrahydro-

Product 1

HCID 156467025,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-oneYield 50.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
180 °C

Procedure

13 g (0.216 mol) of urea are added to 32 g (0.216 mol) of 1,2,3,4-tetrahydroquinolin-8-amine and the mixture is heated for 3 hours at 180° C. Boiling water is added, the reaction mixture is allowed to cool, ether is added and the mixture is stirred for 2 hours. The reaction mixture is then filtered, the precipitate is sucked dry, washed successively with water and ether and dried under vacuum. There are obtained 19 g of product which is recrystallized from isopropanol. The residue is purified by chromatography on a column of silica gel, the eluent being a dichloromethane/methanol (95/5) mixture. There are obtained 7 g of product which is used as is in the following stage.

Workup

  1. temperatureto cool
  2. filtrationThe reaction mixture is then filtered
  3. customthe precipitate is sucked dry
  4. washwashed successively with water and ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-755965265ca44c90bc7d9f6bf00929e3
Source dataset
uspto-grants-1996_12
Patent number
US05589476

Reaction notes

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