Potassium Carbonate → HCID 66851931, compound

HRID 538783Notes

Reaction equation

HRID 538783 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].Br[CH2:15][CH2:16][O:17][CH3:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH2:15][CH2:16][O:17][CH3:18])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 10583428Methyl 5-cyano-2-hydroxybenzoate

Product 1

HCID 66851931HCID 66851931, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 5-cyano-2-hydroxybenzoate (Astatech, 3.0 g, 16.9 mmol), 1-bromo-2-methoxyethane (2.6 g, 18.6 mmol), and K2CO3 (2.3 g, 16.9 mmol) were mixed in 25 mL of DMF and heated at 60° C. for 48 hours. The reaction was diluted with 100 mL of EtOAc washed with water, brine, dried with MgSO4 and the solvent removed to provide the title compound. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 3.46 (s, 3H) 3.79-3.84 (m, 2H) 3.90 (s, 3H) 4.23-4.28 (m, 2H) 7.07 (d, J=8.82 Hz, 1H) 7.72 (dd, J=8.65, 2.20 Hz, 1H) 8.11 (d, J=2.37 Hz, 1H). MS (DCI/NH3) m/z 236.0 (M+H)+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried with MgSO4
  3. customthe solvent removed

Sources & evidence

ORD record
ord-ea1480d8fa6c4a81a215361827f2dab4
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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