Chloroacetyl chloride → 2-Chloro-N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

HRID 1045654Notes

Reaction equation

HRID 1045654 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].Cl.[NH2:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].C(N(CC)CC)C>O1CCCC1>[Cl:1][CH2:2][C:3]([NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 124805352-Amino-3,4-dihydronaphthalen-1(2H)-one--hydrogen chloride (1/1)

Product 1

HCID 132930622-Chloro-N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamideYield 39.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chloroacetyl chloride (14 g, 124 mmol) was added to a solution of 2-amino-3,4-dihydro-2H-naphthalen-1-one hydrochloride (16 g, 81 mmol) and triethylamine (41 g, 405 mmol) in tetrahydrofuran (600 ml) and the mixture was stirred for one hour. The solution was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform) to afford 2-chloro-N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide (7.58 g, 31.9 mmol, 39%) as white crystals.

Workup

  1. customThe solution was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform)

Sources & evidence

ORD record
ord-5bd7b247df824985865976207bd60229
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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