Quinoline → 4-Chloro-1-benzothiophene

HRID 1500541Notes

Reaction equation

HRID 1500541 reaction equation
C([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([Cl:13])[C:6]=2[CH:5]=1)(O)=O.N1C2C(=CC=CC=2)C=CC=1>C(OC(C)C)(C)C.[Cu]>[Cl:13][C:12]1[C:6]2[CH:5]=[CH:4][S:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 38545164-Chlorobenzo(b)thiophene-2-carboxylic Acid

Product 1

HCID 123986054-Chloro-1-benzothiophene

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-carboxy-4-chlorobenzo[b]thiophene (7.24 g), quinoline (36 ml), and copper powder (1.45 g) was stirred at 145 to 155° C. for 1 hour. After the mixture was allowed to cool to room temperature, the mixture was diluted with diisopropyl ether (145 ml), and insoluble materials were removed by filtration. The filtrate was washed with dilute hydrochloric acid (40 ml of 35% concentrated hydrochloric acid+200 ml of cold water) and with water, then dried over magnesium sulfate, and concentrated. A trace amount of precipitates was further removed from the concentrate by filtration to obtain 4-chlorobenzo[b]thiophene.

Workup

  1. temperatureto cool to room temperature
  2. customwere removed by filtration
  3. washThe filtrate was washed with dilute hydrochloric acid (40 ml of 35% concentrated hydrochloric acid+200 ml of cold water) and with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customA trace amount of precipitates
  7. customwas further removed from the
  8. concentrationconcentrate by filtration

Sources & evidence

ORD record
ord-a951a2f9655246088820bc4afc685ec8
Source dataset
uspto-grants-2015_12
Patent number
US09206169B2

Reaction notes

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