Chlorosuccinimide → 2-Chloro-3-quinolin-6-ylbutanal

HRID 500232Notes

Reaction equation

HRID 500232 reaction equation
N1CCC[C@H]1C(O)=O.[N:9]1[C:18]2[C:13](=[CH:14][C:15]([CH:19]([CH3:23])[CH2:20][CH:21]=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.[Cl:24]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:24][CH:20]([CH:19]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:9]=[CH:10][CH:11]=[CH:12]2)[CH3:23])[CH:21]=[O:22]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 145742L-ProlineHCID 866215133-Quinolin-6-ylbutanal

Product 1

HCID 866215142-Chloro-3-quinolin-6-ylbutanalYield 82.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

L-Proline (5.8 mg, 0.050 mmol) was added to a solution of 3-quinolin-6-ylbutanal (50 mg, 0.25 mmol) in chloroform (0.5 mL) at 0° C. followed by addition of N-chlorosuccinimide (36.9 mg, 0.276 mmol). The mixture was stirred at RT for 2 h, diluted with hexanes and filtered. The filtrate was concentrated and purified by chromatography on silica gel with EtOAc in methylene chloride (0-10%) to afford the desired product (0.048 g, 82%). LCMS: (M+H)=234.1/236.1.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by chromatography on silica gel with EtOAc in methylene chloride (0-10%)

Sources & evidence

ORD record
ord-2b946147b3a14c32b5a1bac72515382a
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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