Ethanolamine → HCID 58257766, compound

HRID 2075670Notes

Reaction equation

HRID 2075670 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([I:12])[CH:8]=2)[N:3]=1.[CH2:13]([CH2:15][NH2:16])O.S(Cl)(Cl)=O>>[I:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]1[CH2:13][CH2:15][N:16]=[C:2]1[CH:11]=[CH:10]2

Participants

4

Reactant 3

HCID 700EthanolamineHCID 24386Thionyl ChlorideHCID 198986972-Chloro-6-iodo-quinoline

Product 1

HCID 58257766HCID 58257766, compound

Conditions

Temperature
50 °C

Procedure

2-Chloro-6-iodo-quinoline (200 mg, 0.69 mmol) and ethanolamine (1 mL) were heated at 130° C. for 1 hour. The reaction was cooled and purified by silica gel chromatography (4:1 EtOAc:Hex), and the isolated product was dissolved in CHCl3. Thionyl chloride (0.12 mL, 1.65 mmol) was added, and the reaction was heated at 50° C. for 1 hour. The reaction was quenched with methanol and basified with saturated aqueous Na2CO3. The mixture was extracted with CH2Cl2, and the combined organic layers were combined, dried, filtered, and concentrated to give the desired product, 2a.

Workup

  1. temperatureThe reaction was cooled
  2. custompurified by silica gel chromatography (4:1 EtOAc:Hex)
  3. dissolutionthe isolated product was dissolved in CHCl3
  4. customThe reaction was quenched with methanol
  5. extractionThe mixture was extracted with CH2Cl2
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-78afbcd790f149ff868370ee2109d71c
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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