Acetamide → 2-(3-Chloro-8-dimethylaminomethyl-naphthalen-2-yl)-acetamide

HRID 505240Notes

Reaction equation

HRID 505240 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].[Cl:5][C:6]1[C:7](CC#N)=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:16][N:17]([CH3:19])[CH3:18]>C1COCC1.O.[Pd](Cl)Cl>[Cl:5][C:6]1[C:7]([CH2:2][C:1]([NH2:4])=[O:3])=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:16][N:17]([CH3:19])[CH3:18]

Participants

6

Reactant 2

HCID 178AcetamideHCID 66882331(3-Chloro-8-dimethylaminomethyl-naphthalen-2-yl)-acetonitrile

Product 1

HCID 668825502-(3-Chloro-8-dimethylaminomethyl-naphthalen-2-yl)-acetamide

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium(II)-chloride (4.3 mg, 0.024 mmol, 0.1 equiv) and acetamide (60 mg, 1.0 mmol, 4.2 equiv) were added to a solution of (3-chloro-8-dimethylaminomethyl-naphthalen-2-yl)-acetonitrile in THF (0.75 ml) and water (0.25 ml). After 18 hours at room temperature, the reaction mixture was adsorbed on silica gel, concentrated to dryness, and purified via two flash columns. Since purification on silica gel failed to remove unreacted acetamide, the resulting mixture was used directly in the next step. MS (ES+): 277 (M+H)+.

Workup

  1. concentrationconcentrated to dryness
  2. custompurified via two flash columns
  3. customSince purification on silica gel
  4. customto remove unreacted acetamide

Sources & evidence

ORD record
ord-95143d33dd0542728045f23e38c89a27
Source dataset
uspto-grants-2010_08
Patent number
US07781438B2

Reaction notes

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