2-Chloro-4-ethoxyquinoline → HCID 178466943, compound

HRID 1415518Notes

Reaction equation

HRID 1415518 reaction equation
Cl[C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:15][CH2:16][CH2:17][S:18][CH2:19][C:20]1[NH:24][CH:23]=[N:22][C:21]=1[CH3:25]>>[CH3:25][C:21]1[N:22]=[CH:23][NH:24][C:20]=1[CH2:19][S:18][CH2:17][CH2:16][NH:15][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 8174292-Chloro-4-ethoxyquinolineHCID 178433288HCID 178433288, compound

Product 1

HCID 178466943HCID 178466943, compoundYield 30.3%

Procedure

2-Chloro-4-ethoxyquinoline (3.72 gms) and 5-(2-aminoethyl)thiomethyl-4-methylimidazole (3.1 g.) were heated together at 150°-160° C (oil-bath temperature) for 3 hours. The residue, on cooling, was washed with water and dried. Purification was effected by column chromatography (silica gel column, ethyl acetate-5% methanol eluant) and crystallisation from acetone to give 2-[2-(4-methyl-5-imidazolylmethylthio)ethylamino]-4-ethoxyquinoline (1.86 gms) m.p. 152.5°-153.5° C.

Workup

  1. temperatureThe residue, on cooling
  2. washwas washed with water
  3. customdried
  4. customPurification
  5. customwas effected by column chromatography (silica gel column, ethyl acetate-5% methanol eluant) and crystallisation from acetone

Sources & evidence

ORD record
ord-622a88482d5c4cf09e1373595afce070
Source dataset
uspto-grants-1977_01
Patent number
US04005205

Reaction notes

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