Hydrochloric Acid → 2,3-Dihydro-1,4-benzodioxin-5-amine

HRID 656911Notes

Reaction equation

HRID 656911 reaction equation
[N+:1]([C:4]1[C:13]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.Cl>C(O)C.[Pd]>[O:9]1[C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([NH2:1])[C:13]=2[O:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 122313185-Nitro-2,3-dihydro-1,4-benzodioxine

Product 1

HCID 117883872,3-Dihydro-1,4-benzodioxin-5-amineYield 102%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Nitro-2,3-dihydro-1,4-benzodioxin (5.4 g; 29.83 mmol) was dissolved in ethanol (130 ml) and conc.HCl added (1.13 ml; 29.83 mmol) this was then stirred with 10% Pd/C under hydrogen at rt and atmospheric pressure overnight. The catalyst was then filtered off and washed with MeOH. The solvents were removed and the crude purified by SCX. Fractions containing product were concentrated to give the desired product (4.6 g).

Workup

  1. customatmospheric pressure overnight
  2. filtrationThe catalyst was then filtered off
  3. washwashed with MeOH
  4. customThe solvents were removed
  5. customthe crude purified by SCX
  6. additionFractions containing product
  7. concentrationwere concentrated

Sources & evidence

ORD record
ord-b430d997319a4934bbdcb908b033d44c
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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