Chloroacetyl chloride → HCID 21491380, compound

HRID 1404901Notes

Reaction equation

HRID 1404901 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2.[Cl:12][CH2:13][C:14](Cl)=[O:15].CCN(CC)CC>C(Cl)Cl>[Cl:12][CH2:13][C:14]([N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1])[CH2:7][CH2:8][CH2:9]1)=[O:15]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 27741668-Methyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 21491380HCID 21491380, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 8-methyl-1,2,3,4-tetrahydroquinoline (1) (2.77 g, 18.8 mmol) in dry CH2Cl2 (50 mL) at 0° C. was added chloroacetyl chloride (1.80 mL, 22.6 mmol) followed by dropwise addition of Et3N (6.30 mL, 45.2 mmol). The reaction was stirred overnight under N2. The reaction mixture was then diluted with CH2Cl2 (50 mL), washed with water (2×15 mL), and saturated NaCl (15 mL). Dried over MgSO4, filtered, and concentrated to give compound 2 (3.7 g). This crude material was used in subsequent reactions without further purification.

Workup

  1. washwashed with water (2×15 mL), and saturated NaCl (15 mL)
  2. dry with materialDried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7fb6809d696d45f38035b07d74a1765d
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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