Methanol → HCID 11516399, compound

HRID 1743339Notes

Reaction equation

HRID 1743339 reaction equation
[Br-:1].[CH2:2]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([NH3+])=[CH:15][CH:14]=2)=[N:8][CH:9]=1)[CH3:3].[CH3:20][OH:21].N([O-])=[O:23].[Na+].C(#N)[CH:27]=[CH2:28]>Br.O.CC(C)=O>[Br:1][CH:27]([CH2:28][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([CH2:2][CH3:3])=[CH:9][N:8]=2)=[CH:14][CH:15]=1)[C:20]([OH:23])=[O:21]

Participants

8

Reactant 4

HCID 887MethanolHCID 7855AcrylonitrileHCID 22239054HCID 22239054, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11516399HCID 11516399, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 260Hydrogen BromideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(2-(5-ethyl-2-pyridyl)ethoxy)phenylammonium bromide (52.8 mmol) in hydrobromic acid (prepared by hydrolyzing 4-(2-(5-ethyl-2-pyridyl)ethoxy)acetanilide according to Example 1c) 25 ml of 48% hydrobromic acid, 50 ml of methanol, 100 ml of acetone are added and the mixture is cooled to 0° C. A solution of sodium nitrite (4.5 g) in water (10 ml) is added dropwise to the mixture at 0 to 5° C. The mixture is mixed at 5° C. for another 20 mins, then acrylonitrile (16.8 ml) is added and the temperature is elevated to 38° C. Cuprous oxide (0.5 g) is added in small portions. The mixture is agitated until release of nitrogen stops, then concentrated under reduced pressure, the concentrate is alkalified by adding an aqueous ammonia solution and extracted with ethyl acetate. The ethylacetate layer is washed with water and dried over sodium sulfate. Evaporating the solvent gives the nitrile of 2-bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]-propionic acid as crude oil (18.7 g, 99% of theory).

Workup

  1. additionThe mixture is mixed at 5° C. for another 20 mins
  2. customis elevated to 38° C
  3. concentrationconcentrated under reduced pressure
  4. additionby adding an aqueous ammonia solution
  5. extractionextracted with ethyl acetate
  6. washThe ethylacetate layer is washed with water
  7. dry with materialdried over sodium sulfate
  8. customEvaporating the solvent

Sources & evidence

ORD record
ord-ade7b421f80b4d70afaef0fd04de8598
Source dataset
uspto-grants-2006_03
Patent number
US07009057B2

Reaction notes

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