Triethylamine → N-Propionyl 1-amino-4-chloronaphthalene

HRID 1761278

Reaction equation

HRID 1761278 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>ClCCl.C(OCC)(=O)C>[C:20]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:12])=[CH:4][CH:3]=1)(=[O:23])[CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 784084-Chloronaphthylamine

Product 1

HCID 22595085N-Propionyl 1-amino-4-chloronaphthaleneYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-amino-4-chloronaphthalene (0.70 g, 3.9 mmol) in dichloromethane (50 ml) was added triethylamine (1.0 ml, 7 mmol), followed by propionyl chloride (0.5 ml, 5.8 mmol). After 20 min the mixture was diluted with ethyl acetate (150 ml) and washed with 2N HCl (100 ml) followed by saturated sodium carbonate (100 ml). The organic phase was separated, dried (MgSO4) and the solvent removed in vacuo. The residue was triturated with a mixture of ethyl acetate and heptane, 130 ml, 3:10) to give 0.62 g (67%) of the desired compound as a white solid.

Workup

  1. washwashed with 2N HCl (100 ml)
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with a mixture of ethyl acetate and heptane, 130 ml, 3:10)

Sources & evidence

ORD record
ord-34a6d0fe94804616bb4845074d70fbfb
Source dataset
uspto-grants-2005_01
Patent number
US06846953B1

Linked notes

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