Sodium Hydroxide → 1-(8-Amino-7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)ethanone

HRID 963363Notes

Reaction equation

HRID 963363 reaction equation
[Cl:1][C:2]1[C:3]([NH:15]C(C)=O)=[C:4]2[O:14][CH2:13][CH2:12][O:11][C:5]2=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[OH-].[Na+]>CO>[NH2:15][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8](=[O:10])[CH3:9])=[C:5]2[O:11][CH2:12][CH2:13][O:14][C:4]=12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19081896N-(8-Acetyl-6-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)acetamide

Product 1

HCID 190818271-(8-Amino-7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)ethanoneYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5'-chloro-2',3'-ethylenedioxy-4'-(methylcarbonylamino)-acetophenone (152 mg, 0.56 mmol) and sodium hydroxide (4N, 1.4 mL, 5.6 mmol) in 5 mL of methanol was heated at reflux for 3.5 hours. The mixture was concentrated by rotary evaporation and the residue was stirred into water. The residue was isolated by filtration and washed with water. Drying gave 4'-amino-5'-chloro-2',3'-ethylenedioxyacetophenone (95 mg, 0.41 mmol), m.p. 133°-136° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. concentrationThe mixture was concentrated by rotary evaporation
  4. customThe residue was isolated by filtration
  5. washwashed with water
  6. customDrying

Sources & evidence

ORD record
ord-5964e31b56e34cfe84f08231b242d820
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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