Ethanol → HCID 12230410, compound

HRID 1356290Notes

Reaction equation

HRID 1356290 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:11](Cl)([C:13](Cl)=[O:14])=[O:12].[CH3:17][CH2:18][OH:19]>C1COCC1>[CH2:18]([O:19][C:13](=[O:14])[C:11]([C:4]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[Cl:1])[NH:6][CH:5]=1)=[O:12])[CH3:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 913454-Chloroindole

Product 1

HCID 12230410HCID 12230410, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloroindole (5.00 g, 33.0 mmol) in dry THF (0.2 L), at 0° C. under argon was added (COCl)2 (3.6 mL, 40.4 mmol). The reaction mixture was stirred overnight while warming to rt, cooled to 0° C., and EtOH (4 mL, 69 mmol) was added. The reaction mixture was stirred at rt overnight, then partitioned between cold 0.2 M aq HCl and EtOAc. The aqueous layer was separated and re-extracted with EtOAc. The EtOAc extracts were washed with saturated aqueous NaHCO3 and brine. The extracts were dried, filtered, and concentrated to give a solid. The solid was purified by silica chromatography to give the title compound: TLC Rf=0.40 (19:1 CH2Cl2/Me2CO); MS (ESI+) m/z 274.0; 1H NMR (300 MHz, CDCl3) δ 9.22 (1H), 8.26 (1H), 7.36 (1H), 7.31 (1H), 7.22 (1H), 4.71 (2H), 1.41 (3H).

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe reaction mixture was stirred at rt overnight
  3. custompartitioned between cold 0.2 M aq HCl and EtOAc
  4. customThe aqueous layer was separated
  5. extractionre-extracted with EtOAc
  6. washThe EtOAc extracts were washed with saturated aqueous NaHCO3 and brine
  7. customThe extracts were dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a solid
  11. customThe solid was purified by silica chromatography

Sources & evidence

ORD record
ord-745efd665f68449d862a3350fbacc653
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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