Acetic Acid → 6-(aminomethyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one acetate

HRID 733509Notes

Reaction equation

HRID 733509 reaction equation
[CH3:1][C:2]1([CH3:15])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:5]=2[C:4](=[O:14])[O:3]1.C(O)(=O)C.N#N>CO.[Pd]>[C:2]([OH:7])(=[O:3])[CH3:1].[NH2:13][CH2:12][C:10]1[CH:9]=[CH:8][C:6]2[O:7][C:2]([CH3:15])([CH3:1])[O:3][C:4](=[O:14])[C:5]=2[CH:11]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 947NitrogenHCID 597024522,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbonitrile

Product 1

HCID 674204786-(aminomethyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one acetateYield 74.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbonitrile (12 g, 0.06 mol) in methanol (500 mL) was added glacial acetic acid (3.5 g, 0.059 mol) and passed N2 for 30 min. To this was added Pd/C (2.4 g, 20%) and hydrogenated under 2 Bars of pressure for 22 h. The reaction mixture was filtered through celite and filtrate concentrated under vacuum. To the solid was added EtOAc (200 mL), stirred for 20 h and filtered. The solid was dried under vacuum to give 6-(aminomethyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one acetate (6 g, 38%). TLC:CHCl3/MeOH, 9:1, Rf: 0.15

Workup

  1. customfor 30 min
  2. filtrationThe reaction mixture was filtered through celite and filtrate
  3. concentrationconcentrated under vacuum
  4. additionTo the solid was added EtOAc (200 mL)
  5. filtrationfiltered
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-d5ce6e851b2c42b3818156b884638008
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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