Cesium carbonate → 1-[2-Amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone

HRID 1422523Notes

Reaction equation

HRID 1422523 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][CH:21]([O:24][CH3:25])[O:22][CH3:23]>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH2:20][CH:21]([O:24][CH3:25])[O:22][CH3:23])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 574451951-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanone

Product 1

HCID 574451961-[2-Amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanoneYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

1-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanone (15.5 g, 83.8 mmol), Cs2CO3 (54.6 g, 167 mmol) and 2-bromo-1,1-dimethoxy-ethane (14.78 mL, 126 mmol) was dissolved in DMF (125 mL) under an atmosphere of nitrogen. The reaction was heated to 65° C. for 6 hours. The reaction was determined to be complete by LC/MS. The reaction was taken up in EtOAc (500 mL) and washed with 5% LiCl(aq) (3×250 mL). Organics were dried over Na2SO4, filtered and solvent removed under reduced pressure. 1-[2-Amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone (12.99 g, 57%) was isolated by silica gel chromatography as a white solid.

Workup

  1. washwashed with 5% LiCl(aq) (3×250 mL)
  2. dry with materialOrganics were dried over Na2SO4
  3. filtrationfiltered
  4. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-fcf4ee8fc7ca442cb5dc7a0ed0ca3d55
Source dataset
uspto-grants-2015_01
Patent number
US08927484B2

Reaction notes

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