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

HRID 902768Notes

Reaction equation

HRID 902768 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 the title compound (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-92ab9ae019f1428681d09fc226c72fd6
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Reaction notes

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