2-Naphthylamine → 2-((1,1-Dimethylethoxycarbonyl)methyl)aminonaphthalene

HRID 890388Notes

Reaction equation

HRID 890388 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(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CN(C)C=O.O>[CH3:24][C:23]([CH3:26])([O:22][C:20]([CH2:19][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])[CH3:25]

Participants

6

Reactant 3

HCID 70572-NaphthylamineHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 221850082-((1,1-Dimethylethoxycarbonyl)methyl)aminonaphthaleneYield 68.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-aminonaphthalene (985 mg, 6.8 mmol) in N,N-dimethylformamide (DMF) (50 mL) was added potassium carbonate (1.806 g, 13.6 mmol) and tert-butyl bromoacetate (1.4 mL, 9.9 mmol). The resulting reaction mixture was stirred at ambient temperature. After 24 hours, the reaction mixture was diluted with water (200 mL), then extracted by ethyl acetate (150 mL). The organic layer was separated and washed with water (3×100 mL), then dried over sodium sulfate. The solvent was evaporated in vacuo to afford a product as ann yellow oil. Purification of product by flash column on silica gel afforded 2-((1,1-dimethylethoxycarbonyl)methyl)aminonaphthalene (1.2 g).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted by ethyl acetate (150 mL)
  3. customThe organic layer was separated
  4. washwashed with water (3×100 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customto afford a product as ann yellow oil
  8. customPurification of product by flash column on silica gel

Sources & evidence

ORD record
ord-a78a44f7d1e74d9d95389da5ea58876d
Source dataset
uspto-grants-2006_02
Patent number
US06995156B2

Reaction notes

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