Oxygen → 2-(Benzo[d]thiazol-2-yl)quinolin-8-ol

HRID 388191Notes

Reaction equation

OC1C=CC=C2C=1N=CC=C2.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[SH:19].[OH:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([C:31](O)=O)[CH:27]=[CH:26]2.O=O.P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[S:19]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:31]1[C:28]1[CH:27]=[CH:26][C:25]2[C:30](=[C:21]([OH:20])[CH:22]=[CH:23][CH:24]=2)[N:29]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To introduce a benzo[d]thiazol group into an 8-hydroxyquinoline compound, 2-aminothiophenol (123 mg, 1.1 mmol) and 8-hydroxyquinoline-2-carboxylic acid (189 mg, 2 mmol) were dissolved in dry toluene (30 ml) with blown nitrogen to prevent oxidation which is caused by oxygen in air. The solution was heated to 40° C. and phosphorus trichloride (0.1 ml, 1.1 mmol) was slowly added thereto. Then, the reaction solution was heated at 100° C. for 24 hours and allowed to cool. The reaction mixture was extracted with a 20% aqueous sodium carbonate solution, distilled water and dichloromethane, dried and recrystallized with dichloromethane and hexane to yield 2-(benzo[d]thiazol-2-yl)quinolin-8-ol, the compound of Formula 1 as a light green solid (yield: 75%).

Workup

temperatureThen, the reaction solution was heated at 100° C. for 24 hours
temperatureto cool
extractionThe reaction mixture was extracted with a 20% aqueous sodium carbonate solution
distillationdistilled water and dichloromethane
customdried
customrecrystallized with dichloromethane and hexane

Sources & evidence

ORD record: ord-d4ab3e0f1b6c43559bd78b8005c6129b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377698B2

Reaction notes

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