Ammonia → 2,2,8-Trimethyl-4H-(1,3)dioxino(4,5-c)pyridine-5-carboxamide

HRID 1158959Notes

Reaction equation

HRID 1158959 reaction equation
[NH3:1].[CH3:2][C:3]1([CH3:16])[O:15][C:7]2[C:8]([CH3:14])=[N:9][CH:10]=[C:11]([CH:12]=[O:13])[C:6]=2[CH2:5][O:4]1.CO>C(O)(C)C.[O-2].[O-2].[Mn+4]>[CH3:2][C:3]1([CH3:16])[O:15][C:7]2[C:8]([CH3:14])=[N:9][CH:10]=[C:11]([C:12]([NH2:1])=[O:13])[C:6]=2[CH2:5][O:4]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 156199462,2,8-trimethyl-4H-(1,3)dioxino(4,5-c)pyridine-5-carbaldehyde

Product 1

HCID 2662792,2,8-Trimethyl-4H-(1,3)dioxino(4,5-c)pyridine-5-carboxamideYield 69%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

Ammonia gas was bubbled into a solution of 2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carbaldehyde (31.3 g, 151 mmol) in isopropyl alcohol (2.4 L) at 0° C. for about 30 minutes. Manganese (IV) dioxide (210 g, 7.96 mmol) was added, and the solution was stirred for about 15 hours at room temperature. Excess manganese (IV) dioxide was filtered through a celite pad and washed with isopropyl alcohol. The filtrate was evaporated and washed with diethyl ether, water, and then with methyl alcohol to give 2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carboxylic acid amide (78) (23.1 g, 69% yield) as a light yellow solid.

Workup

  1. filtrationExcess manganese (IV) dioxide was filtered through a celite pad
  2. washwashed with isopropyl alcohol
  3. customThe filtrate was evaporated
  4. washwashed with diethyl ether, water

Sources & evidence

ORD record
ord-7fd38118a48b4c8abb653c84be985ede
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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