Acetyl chloride → N-2-Naphthalenylacetamide

HRID 1270747Notes

Reaction equation

HRID 1270747 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl>[C:19]([NH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 70572-NaphthylamineHCID 8471Triethylamine

Product 1

HCID 11394N-2-Naphthalenylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.05 g (21.3 mmol) of 2-aminonaphthalene and 3.56 mL (25.6 mmol) of triethylamine in 100 mL of CH2Cl2 is cooled to 0° C., and 1.59 mL (22.4 mmol) of acetyl chloride is added dropwise. The reaction is allowed to warm to room temperature and is stirred under an atmosphere of nitrogen for 4 hours. The mixture is diluted with 100 mL of CH2Cl2 and washed with 50 mL each of 1 N HCl, H2O, saturated aqueous NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and the solvent evaporated to give 2-acetylaminonaphthalene as a brown solid.

Workup

  1. washwashed with 50 mL each of 1 N HCl, H2O, saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-9caedf1a7a024afd827574293dc02487
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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