Diethyl Ether → HCID 178507700, compound

HRID 1168493Notes

Reaction equation

HRID 1168493 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14]CC)=O)=[C:7]2[OH:17].[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1.CCOCC>O>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([NH:31][CH2:30][C:29]1[CH:32]=[CH:33][C:26]([Cl:25])=[CH:27][CH:28]=1)=[O:14])=[C:7]2[OH:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 660364-ChlorobenzylamineHCID 178469661HCID 178469661, compound

Product 1

HCID 178507700HCID 178507700, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of ethyl 8-amino-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxylate (Preparation 2, 1.0 g) and 4-chlorobenzylamine (4 mL) is heated at 180° C. The solution is cooled and stirred with ether (6 mL) and water (6 mL). The resulting precipitate is removed by filtration, washed with water followed by ether and dried to afford 1.05 g of the title compound. Physical characteristics: 1H NMR (DMSO-d6) δ2.35, 3.45, 3.57, 4.54, 5.65, 7.02, 7.39, 8.62, 10.6, 11.1.

Workup

  1. temperatureThe solution is cooled
  2. customThe resulting precipitate is removed by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-176b776f23904bd8ad79abb49bcd52fd
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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