Chloroacetyl chloride → 2-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one

HRID 1942244Notes

Reaction equation

HRID 1942244 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Cl:11][CH2:12][C:13](Cl)=[O:14].C(N(CC)CC)C>C(Cl)Cl>[Cl:11][CH2:12][C:13]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:14]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 2401372-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-oneYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,2,3,4-tetrahydroquinolin (3) (2.00 g, 15.0 mmol) in dry CH2Cl2 (30 mL) at 0° C. was added chloroacetyl chloride (1.27 mL, 16.0 mmol) followed by drop wise addition of triethylamine (2.50 mL, 18.03 mmol). The reaction was stirred overnight under N2. The reaction mixture was then diluted with CH2Cl2 (50 mL), washed with 5% HCl (15 mL), H2O (2×15 mL) and brine. Dried over MgSO4, filtered and concentrated to give 3.05 g of 4. This crude material was used in subsequent reactions without further purification.

Workup

  1. washwashed with 5% HCl (15 mL), H2O (2×15 mL) and brine
  2. dry with materialDried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6d926f0863e64cffbc921ce075601bbd
Source dataset
uspto-grants-2013_03
Patent number
US08389546B2

Reaction notes

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