Hydrogen Bromide → 4-(2-aminoethyl)pyridin-2(1H)-one hydrobromide

HRID 1410035Notes

Reaction equation

HRID 1410035 reaction equation
Cl.C[O:3][C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][NH2:12])[CH:7]=[CH:6][N:5]=1.[BrH:13]>CC(O)=O>[BrH:13].[NH2:12][CH2:11][CH2:10][C:8]1[CH:7]=[CH:6][NH:5][C:4](=[O:3])[CH:9]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 683793082-(2-Methoxypyridin-4-yl)ethanamine hydrochloride

Product 1

HCID 683793994-(2-aminoethyl)pyridin-2(1H)-one hydrobromideYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(2-methoxypyridin-4-yl)ethanamine hydrochloride (0.8 g, 4.23 mmol) was dissolved in 45% HBr (7 mL) and HOAc (7 mL). The mixture was heated to reflux for 4 hours and then the solvent was removed under reduce pressure. The residue was washed with THF (20 mL) and dried to give 4-(2-aminoethyl)pyridin-2(1H)-one hydrobromide (0.8 g 86%) as a grey solid. LC-MS: 139 [M+H]+, tR=0.28 min.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customthe solvent was removed
  4. washThe residue was washed with THF (20 mL)
  5. customdried

Sources & evidence

ORD record
ord-f3cbf7ae89d744678d639116cf720e9f
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

Loading…