Cesium carbonate → HCID 18789594, compound

HRID 618219Notes

Reaction equation

HRID 618219 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:17][C:18]#[N:19]>CC(CC)=O>[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:17][C:18]#[N:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 1044482-Amino-o-cresol

Product 1

HCID 18789594HCID 18789594, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-methyl-3-aminophenol (20.1 g, 0.163 mol) was dissolved in methylethylketone (MEK) (150 ml). Cesium carbonate (106 g, 0.326 mmol) was added in portions followed by dropwise addition of bromoacetonitrile (29.3 g, 0.245 mol) over 30 min. The mixture was stirred 14 hr at room temperature, then filtered through a coarse fritted funnel. The solids were washed with ethylacetate (2×100 ml) and the combined washings and filtrate were concentrated at reduced pressure to give 20.8 g (79% yield) of (2-methyl-3-aminophenoxy)acetonitrile which required no further purification.

Workup

  1. filtrationfiltered through a coarse fritted funnel
  2. washThe solids were washed with ethylacetate (2×100 ml)
  3. concentrationthe combined washings and filtrate were concentrated at reduced pressure

Sources & evidence

ORD record
ord-4107e1296b4f4e89b419a7d21a753de8
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

Loading…