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

HRID 904815Notes

Reaction equation

HRID 904815 reaction equation
C(=O)(O)[O-].[Na+].C(OCC)(=O)C.Cl.[NH2:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].[Cl:25][CH2:26][C:27](Cl)=[O:28]>O>[Cl:25][CH2:26][C:27]([NH:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24])=[O:28]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 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 568%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of sodium bicarbonate (4.0 g) in water (50 ml) layered with ethyl acetate (200 ml) was added solid 2-amino-3,4-dihydronaphthalen-1(2H)-one hydrochloride (4.0 g, 2 mmol). After the solid had dissolved chloroacetylchloride (1.6 ml, 2 mmol) was added dropwise over 10 minutes. After stirring for 1 hr, the ethyl acetate layer was separated, washed with brine and dried over Na2SO4. Evaporation afforded 2.7 g (57%) of a dark solid; m.p. 118°-122° C. The product was purified by chromatography on silica using ethyl acetate: hexane (1:1 v/v) to elute, m.p. 121°-123° C.

Workup

  1. additionwas added dropwise over 10 minutes
  2. customthe ethyl acetate layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation

Sources & evidence

ORD record
ord-2de9076b90ed4f9395257f24d5d3565e
Source dataset
uspto-grants-1983_12
Patent number
US04420480

Reaction notes

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