Chlorosuccinimide → 2-Chloro-3-(quinolin-6-yl)propanal

HRID 452043Notes

Reaction equation

HRID 452043 reaction equation
N1CCC[C@H]1C(O)=O.[N:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH:21]=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.[Cl:23]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:23][CH:20]([CH2:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:9]=[CH:10][CH:11]=[CH:12]2)[CH:21]=[O:22]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 145742L-ProlineHCID 229313103-(Quinolin-6-yl)propanal

Product 1

HCID 575165372-Chloro-3-(quinolin-6-yl)propanal

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

L-Proline (410 mg, 3.5 mmol) was added to a solution of 3-quinolin-6-ylpropanal (3.27 g, 17.6 mmol, Example 1, Step 6) in chloroform (39 mL) at 0° C. followed by addition of N-chlorosuccinimide (2.48 g, 18.5 mmol) and the reaction mixture was slowly warmed to ambient temperature and stirred for 1 h, monitoring by LCMS. The solvent was concentrated under reduced pressure and the residue was purified on a silica gel column with ethyl acetate in hexane (0-50%) to give the desired product. (95%) LCMS: (M+H+ H2O)=237.9/239.9.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customthe residue was purified on a silica gel column with ethyl acetate in hexane (0-50%)

Sources & evidence

ORD record
ord-e750c83877b246f6b46bdcba2191e97d
Source dataset
uspto-grants-2013_07
Patent number
US08487096B2

Reaction notes

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