Dimethylformamide → Ethyl 1-naphthylaminoacetate

HRID 1934806Notes

Reaction equation

HRID 1934806 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:19]1([NH2:29])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1>CCCCCC.C(OCC)(=O)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][NH:29][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[CH3:18]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 86401-NaphthylamineHCID 11430Potassium Carbonate2×

Product 1

HCID 18347840Ethyl 1-naphthylaminoacetateYield 75%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

19.3 g(139 mmol) of potassium carbonate was added to 200 ml of dimethylformamide, and then the solution was heated to dissolve potassium carbonate. After cooling to room temperature, 8 ml(70 mmol) of ethyl bromoacetate and 10 g(70 mmol) of 1-naphthylamine were added to the solution, which was then stirred for 48 hours. DMF was removed under reduced pressure and ethyl acetate was added to the residue. The ethyl acetate layer was washed with water 4 times and saturated sodium chloride solution. Ethyl acetate was removed under reduced pressure, and then column chromatography was performed using a mixed solution(9:1) of hexane and ethyl acetate as an eluent to obtain 12 g of the title compound(Yield 75%, MW 229).

Workup

  1. temperaturethe solution was heated
  2. customDMF was removed under reduced pressure and ethyl acetate
  3. additionwas added to the residue
  4. washThe ethyl acetate layer was washed with water 4 times and saturated sodium chloride solution
  5. customEthyl acetate was removed under reduced pressure

Sources & evidence

ORD record
ord-908c29f6af164d959dfdd0526986404b
Source dataset
uspto-grants-2002_05
Patent number
US06384061B1

Reaction notes

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