D-Proline → 2-Chloro-3-quinoxalin-6-ylpropanal

HRID 500191Notes

Reaction equation

HRID 500191 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][CH2:12][CH:13]=[O:14])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.N1CCC[C@@H]1C(O)=O.[Cl:23]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:23][CH:12]([CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[N:4]2)[CH:13]=[O:14]

Participants

6

Reactant 3

HCID 8988D-ProlineHCID 31398ChlorosuccinimideHCID 866215076-Quinoxalinepropanal

Product 1

HCID 623955372-Chloro-3-quinoxalin-6-ylpropanalYield 95%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 3-quinoxalin-6-ylpropanal (0.195 g, 0.00105 mol) in chloroform (3 mL) was added D-proline (24 mg, 0.00021 mol) followed by N-chlorosuccinimide (147 mg, 0.00110 mol). The mixture was stirred at 0° C. for 2 h, and then at RT overnight. The mixture was diluted with methylene chloride. The solution was washed with water, brine, dried over Na2SO4, filtered, and concentrated to yield the desired product (220 mg, 95%). LCMS: (M+H)=221.3.

Workup

  1. customat RT
  2. customovernight
  3. washThe solution was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ff4014db871d4085ba2417b122a47104
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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