7-(azidomethyl)-2H,3H-[1,4]dioxino[2,3-c]pyridine → 1-(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-yl)methanamine

HRID 2193125Notes

Reaction equation

HRID 2193125 reaction equation
[N:1]([CH2:4][C:5]1[N:10]=[CH:9][C:8]2[O:11][CH2:12][CH2:13][O:14][C:7]=2[CH:6]=1)=[N+]=[N-]>[C].[Pd].C(O)C>[O:14]1[C:7]2[CH:6]=[C:5]([CH2:4][NH2:1])[N:10]=[CH:9][C:8]=2[O:11][CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 593983647-(azidomethyl)-2H,3H-[1,4]dioxino[2,3-c]pyridine

Product 1

HCID 593981871-(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-yl)methanamine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To 10 mL of an ethanol solution containing 0.53 g of 7-(azidomethyl)-2,3-dihydro-(1,4)dioxino(2,3-c)pyridine, 0.10 g of 5% palladium-carbon was added at room temperature, and the mixture was stirred for 1 hour and 45 minutes under a hydrogen atmosphere. The insoluble material filtered off, and the solvent was removed under reduced pressure to obtain 0.46 g of a brown oily substance, 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-yl)methaneamine.

Workup

  1. additionwas added at room temperature
  2. filtrationThe insoluble material filtered off
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dceccc58263541bd9ff481cc4f7068f6
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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