Cesium carbonate → HCID 18789594, compound

HRID 1106725Notes

Reaction equation

HRID 1106725 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-f0c6bb434937423787bd896b57c5022c
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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