Water → HCID 59474753, compound

HRID 1966529Notes

Reaction equation

HRID 1966529 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:18][NH2:19].O>CS(C)=O>[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:18][NH:19][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1608Benzenemethanamine, 3,4-dichloro-HCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 59474753HCID 59474753, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Chloro-8-hydroxy-2-methylquinoline (500 mg, 2.58 mmole) and 3,4-dichlorobenzylamine (910 mg, 5.16 mmole) in dimethylsulfoxide (5 mL) were stirred at 140° C. for 90 min in a microwave oven. Water was added and the mixture was decanted to obtain an oily residue. The residue was washed with ethyl acetate to give a brownish solid (350 mg, 41%). ESI-MS [M+H]+=333.1/337.0 calculated for C17H14Cl2N2O=333 g/mole

Workup

  1. customthe mixture was decanted
  2. customto obtain an oily residue
  3. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-3f4a516d06b34cf4ac45dff82ae12d99
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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