Oxalyl chloride → 2-oxo-2-(2-phenylindolizin-3-yl)acetyl Chloride

HRID 1910837Notes

Reaction equation

HRID 1910837 reaction equation
[C:1]([Cl:6])(=[O:5])[C:2](Cl)=[O:3].[C:7]1([C:13]2[CH:14]=[C:15]3[N:20]([CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16]3)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1.C1COCC1>[O:3]=[C:2]([C:21]1[N:20]2[C:15]([CH:16]=[CH:17][CH:18]=[CH:19]2)=[CH:14][C:13]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:1]([Cl:6])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 961282-Phenylindolizine

Product 1

HCID 50082602-oxo-2-(2-phenylindolizin-3-yl)acetyl ChlorideYield 80%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (2.23 mL, 25.9 mmol) was added to an ice-cold solution of 2-phenylindolizine (4.0 g, 20.7 mmol) in a mixture of toluene (40 mL) and THF (8 mL). The reaction mixture was stirred at r.t. for 5 h then concentrated in vacuo. The residue obtained was recrystallised from DCM-hexane to yield oxo-(2-phenyl-indolizin-3-yl)-acetyl chloride (4.6 g, 80%) as a solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue obtained
  3. customwas recrystallised from DCM-hexane

Sources & evidence

ORD record
ord-89f85fc6af424f4593ad5e01c930841e
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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