Hydrogen Bromide → HCID 22958388, compound

HRID 1924789Notes

Reaction equation

HRID 1924789 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Cl:19])[C:7]([CH:10](C(OC)=O)C(OC)=O)=[N:8][CH:9]=1)(=[O:3])[CH3:2].Br>>[Cl:19][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[N:8][C:7]=1[CH3:10]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 86637416HCID 86637416, compound

Product 1

HCID 22958388HCID 22958388, compoundYield 63%

Conditions

Temperature
120 °C

Procedure

A mixture of dimethyl (5-acetyl-3-chloropyridin-2-yl)malonate (2.18 g, 7.63 mmol) and 48% HBr aq. (10.0 mL) was stirred at 120° C. for 1.5 hours. The mixture was neutralized by the addition of sat.NaHCO3 aq. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, concentrated to give the title compound (810 mg, 63%) as a slight yellow solid. 1H NMR (300 MHz, CDCl3) δ 2.62 (3H, s), 2.71 (6H, s), 8.17 (1H, s), 8.92 (1H, s).

Workup

  1. additionThe mixture was neutralized by the addition
  2. extractionNaHCO3 aq. The mixture was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8ce69af308a048018a4ef1b47720b5e0
Source dataset
uspto-grants-2012_05
Patent number
US08178558B2

Reaction notes

Loading…