HCID 12486248, compound → 3,4-Dihydro-2H-pyrano[3,2-b]pyridine

HRID 712476Notes

Reaction equation

HRID 712476 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][N:6]=1>Br>[O:11]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 12486248HCID 12486248, compound

Product 1

HCID 124862493,4-Dihydro-2H-pyrano[3,2-b]pyridineYield 30.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 2-(3-hydroxypropyl)pyridin-3-ol (0.90 g) in 48% hydrobromic acid (20 mL) in a sealed tube was heated at 150° C. for 5 h. The reaction mixture was cooled to rt, concentrated in vacuo and poured into a solution of NaOH in MeOH (1 M). The mixture was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA) to afford the title compound as pale yellow oil (0.24 g, 30.00%), HPLC: 92.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 136.3 (M+1); 1H NMR (400 MHz, CDCl3) δ: 7.99-7.98 (m, 1H), 7.19-7.11 (m, 2H), 4.19 (t, J=7.8 Hz, 2H), 2.91 (t, J=7.8 Hz, 2H), 2.12-2.07 (m, 2H) ppm.

Workup

  1. concentrationconcentrated in vacuo
  2. additionpoured into a solution of NaOH in MeOH (1 M)
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA)

Sources & evidence

ORD record
ord-5bf74b1301eb4e1cb6adf857c288445b
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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