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

HRID 1404902Notes

Reaction equation

HRID 1404902 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].CCN(CC)CC>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-tetrahydroquinoline (3, 2.00 g, 15.0 mmol) in dry CH2Cl2 (30 mL) at 0° C. was added chloroacetyl chloride (1.80 g, 16.0 mmol) followed by dropwise addition of Et3N (2.50 mL, 18.0 mmol). The reaction was stirred overnight under N2. The reaction mixture was diluted with CH2Cl2 (50 mL), washed with 5% HCl (15 mL), water (2×15 mL), and saturated NaCl (15 mL). 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), water (2×15 mL), and saturated NaCl (15 mL)
  2. dry with materialDried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b1ca94eea0714d2cb36817b7167d5699
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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