N-methyl-2-pyrrolidone → HCID 58729082, compound

HRID 551872Notes

Reaction equation

HRID 551872 reaction equation
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[N:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][OH:20])=[CH:14][CH:13]=1.CN1CCCC1=O>ClCCl>[Br:8][C:6]1[N:7]=[C:2]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][OH:20])=[CH:14][CH:13]=2)[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 669044-Aminophenethyl alcoholHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-one

Product 1

HCID 58729082HCID 58729082, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of 3,5-dibromo-1-methyl-2(1H)pyrazinone (2.0 g; 7.5 mmol), 2-(4-Amino-phenyl)-ethanol (1.0 g; 7.3 mmol), and 1-methyl-2-pyrrolidinone (1 mL) was heated at 120° C. for 1 hr. The mixture was cooled to room temperature, diluted with dichloromethane and filtered to give a dull brown oil. This was dissolved in CH2Cl2 and washed with 0.01N NaOH, and dried over solid sodium sulfate. After filtration and evaporation of the CH2Cl2 layer, the resulting brown solid was chromatographed on silica using methanol/CH2Cl2 (1:9) as eluent to provide 2.0 g of 5-bromo-3-[4-(2-hydroxy-ethyl)-phenylamino]-1-methyl-1H-pyrazin-2-one (1) as a light tan solid. MS 324.23 (M+H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. customto give a dull brown oil
  4. washwashed with 0.01N NaOH
  5. dry with materialdried over solid sodium sulfate
  6. filtrationAfter filtration and evaporation of the CH2Cl2 layer
  7. customthe resulting brown solid was chromatographed on silica

Sources & evidence

ORD record
ord-960e2ee2202e4a4eadc7d535517ea4bc
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

Loading…