N-methyl-2-pyrrolidone → HCID 2775209, compound

HRID 1649032Notes

Reaction equation

HRID 1649032 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([C:11]([C:17](=[O:19])[CH3:18])=[CH:12][C:13]=1[C:14](=[O:16])[CH3:15])[NH:8][CH2:9][CH3:10])C=C.CN1C(=O)[CH2:24][CH2:23][CH2:22]1>C(O)C.[Pd]>[C:17]([C:11]1[CH:12]=[C:13]([C:14](=[O:16])[CH3:15])[C:5]([OH:4])=[C:6]([CH2:22][CH2:23][CH3:24])[C:7]=1[NH:8][CH2:9][CH3:10])(=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 204815281,1'-{4-(Ethylamino)-6-[(prop-2-en-1-yl)oxy]-1,3-phenylene}di(ethan-1-one)

Product 1

HCID 2775209HCID 2775209, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product of step (b) (0.013 mole) was heated in NMP (25 ml) at reflux under nitrogen for 1 hour. After cooling to room temperature, the mixture was diluted with ethanol (25 ml), and hydrogenated over 5% Pd/C at 15-20 psi for 21/2 hours. After filtration, the mixture was poured into water, the grey solid isolated by filtration, and recrystallised from ethanol to give the title compound. Yield 63%, mp 114°-115° C.

Workup

  1. temperatureat reflux under nitrogen for 1 hour
  2. custom2 hours
  3. filtrationAfter filtration
  4. additionthe mixture was poured into water
  5. customthe grey solid isolated by filtration
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-1196540a4a4f44e98255c791c77436c9
Source dataset
uspto-grants-1983_11
Patent number
US04414416

Reaction notes

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