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

HRID 1861997Notes

Reaction equation

HRID 1861997 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.[Cl:13][CH2:14][C:15](Cl)=[O:16]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[Cl:13][CH2:14][C:15]([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:16]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 83588-Amino-2-naphthalenol

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 8-amino-2-naphthol (8.00 g, 50.3 mmol) in 500 mL of EtOAc and 500 mL of saturated NaHCO3 solution at 0° C. was added chloroacetyl chloride (4.40 mL, 55.2 mmol). After 2 hours, the layers were separated, and the aqueous layer was extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The titled product was obtained as a dark brown solid which was used in the next reaction without further purification.

Workup

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

Sources & evidence

ORD record
ord-d93989475f3a410ea77340dc6a0f3df1
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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