HCID 178477333, compound → HCID 178477297, compound

HRID 1893677Notes

Reaction equation

HRID 1893677 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([S:12][CH2:13][CH3:14])[C:8](C(O)=O)=[C:7]2[OH:18]>C1(OC2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([S:12][CH2:13][CH3:14])[CH:8]=[C:7]2[OH:18]

Participants

3

Reactant 1

HCID 178477333HCID 178477333, compound

Product 1

HCID 178477297HCID 178477297, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
250 °C

Procedure

8-Chloro-2-ethylsulfanyl-4-hydroxy-quinoline-3-carboxylic acid (17.17 g, 60.52 mmol) was suspended in diphenyl ether (250 mL) and heated to 250° C. for 30 minutes and the mixture was then cooled down to room temperature. The mixture was directly transferred onto a load cartridge and purified by column chromatography to afford 8-chloro-2-ethylsulfanyl-quinolin-4-ol (12.36 g, 85% yield). 1H NMR (CDCl3, 300 MHz) δ 8.25 (d, 1H), 7.70 (d, 1H), 7.32 (t, 1H), 6.52 (s, 1H), 3.18-3.11 (m, 2H), 1.54-1.44 (m, 3H). LCMS found 240.17 [M+H]+.

Workup

  1. temperaturethe mixture was then cooled down to room temperature
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-c73d6809c5c74bd59992a0171fe45fc6
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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