Azane;hydrate → (2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)methanol

HRID 1804725Notes

Reaction equation

HRID 1804725 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[C:6](=[O:13])[CH:7]=[C:8]([CH2:11][OH:12])O[CH:10]=1.O.[NH3:15]>>[O:13]1[C:6]2[CH:7]=[C:8]([CH2:11][OH:12])[N:15]=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 12896473Azane;hydrateHCID 59510742HCID 59510742, compound

Product 1

HCID 21873770(2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)methanol

Conditions

Temperature
85 °C

Procedure

To 229 g of 5-(2-chloroethoxy)-2-(hydroxymethyl)-4H-pyran-4-one (crude product), 572 mL of 28% ammonia water was added, the mixture was stirred for 7 hours at 85° C. and allowed to stand overnight at room temperature. The reaction mixture was extracted 4 times with 500 mL of 2-propyl acetate. The organic layer was combined therewith and the solvent was evaporated under reduced pressure to give 90.5 g of (2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-yl)methanol as a brown oily substance.

Workup

  1. waitto stand overnight at room temperature
  2. extractionThe reaction mixture was extracted 4 times with 500 mL of 2-propyl acetate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9d52f76a4ef140afbcd6b3bd95a5e772
Source dataset
uspto-grants-2013_01
Patent number
US08354426B2

Reaction notes

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