Hydrochloric Acid → 1-(6-Amino-2H-1,3-benzodioxol-5-yl)-2-chloroethan-1-one

HRID 1743020Notes

Reaction equation

HRID 1743020 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]2[O:11][CH2:12][O:13][C:8]2=[CH:7][C:6]=1[C:14](=[O:17])[CH2:15][Cl:16])(=O)C.Cl>C(O)C>[NH2:4][C:5]1[CH:10]=[C:9]2[O:11][CH2:12][O:13][C:8]2=[CH:7][C:6]=1[C:14](=[O:17])[CH2:15][Cl:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10264361HCID 10264361, compound

Product 1

HCID 104207691-(6-Amino-2H-1,3-benzodioxol-5-yl)-2-chloroethan-1-oneYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2'-acetylamino-4',5'-methylenedioxy-2-chloroacetophenone (0.9 g, 3.53 mmol) or an equivalent amount of 2'-pivoylamino-4',5'-methylenedioxy-2-chloroacetophenone in ethanol (60 mL) at about 5° C. is added, dropwise, conc. HCl (12.5 mL, 149.7 mmol). The reaction mixture is then heated at reflux for about an hour, then poured over 2N NaOH/ice (80 mL/60 g) and washed with ethyl acetate (3×70 mL). The organic portions are combined and washed with brine (50 mL), dried (anhydrous sodium sulfate) and concentrated in vacuo to yield a greenish-yellow solid. This solid is recrystallized from ethyl acetate/isopropanol/hexane, treated with activated charcoal, to yield 2'-amino-4',5'-methylenedioxy-2-chloroacetophenone (0.39 g, 52% of theory).

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureat reflux for about an hour
  3. washwashed with ethyl acetate (3×70 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried (anhydrous sodium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto yield a greenish-yellow solid
  8. customThis solid is recrystallized from ethyl acetate/isopropanol/hexane
  9. additiontreated with activated charcoal

Sources & evidence

ORD record
ord-7b2acad04e4f4e14aeabd584a4ad9a53
Source dataset
uspto-grants-1994_08
Patent number
US05342947

Reaction notes

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