Chloroacetyl chloride → 2-chloro-N-(7-hydroxynaphthalen-1-yl)acetamide

HRID 1862007Notes

Reaction equation

HRID 1862007 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.C([O-])(O)=O.[Na+].[Cl:18][CH2:19][C:20](Cl)=[O:21]>CCOC(C)=O>[Cl:18][CH2:19][C:20]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[CH:5]=[CH:4][CH:3]=1)=[O:21]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 83588-Amino-2-naphthalenolHCID 516892Sodium Bicarbonate

Product 1

HCID 186212152-chloro-N-(7-hydroxynaphthalen-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-amino-2-naphthol (10.0 g, 62.8 mmol) in 240 mL of 1:1 EtOAc/saturated NaHCO3 solution was added chloroacetyl chloride dropwise (5.5 mL, 69.1 mmol). After 20 minutes, the solution was filtered, the layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled product.

Workup

  1. filtrationthe solution was filtered
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d39822667b44bb4bd0a51b8f19d20f7
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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