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

HRID 412169Notes

Reaction equation

HRID 412169 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]>>[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

4

Reactant 3

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

Product 1

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

Procedure

To a solution of 8-amino-2-naphthol (10.0 g, 62.8 mmol) in 240 mL of 1:1EtOAc/saturated NaHCO3 solution was added chloroacetyl chloride dropwise (5.5 mL, 69.1 mmol). After one hour, 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-4a6c1128f4b5445d8e2f9380fd61e864
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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