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Dimethylformamide → 5-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one

HRID 470528
Notes
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Reaction equation

HRID 470528 reaction equation
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=1.C1(CBr)CC1.CN(C)C=O>O1CCCC1.C(OCC)(=O)C>[Br:7][C:8]1[CH:9]=[CH:10][C:11](=[O:14])[N:12]([CH2:1][CH:2]2[CH2:4][CH2:3]2)[CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81503BromomethylcyclopropaneHCID 5995285-Bromo-2-hydroxypyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 596357015-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

KOtBu (0.68 g) was added to a solution of 5-bromo-1H-pyridin-2-one (1.00 g) in tetrahydrofuran (20 mL) at room temperature. After stirring for 30 min, cyclopropylmethyl bromide (0.77 mL) and dimethylformamide (3 mL) were added to the suspension and the resulting mixture was warmed to 70° C. After stirring the mixture at 70° C. for 2 h, the reaction was complete. The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), and washed with water (2×20 mL) and brine (20 mL). Then, the solution was dried (MgSO4) and the solvent was removed to give the title compound as a colorless oil. Yield: 1.18 g (90% of theory). Mass spectrum (ESI+): m/z=228/230 (Br) [M+H]+

Workup

  1. stirringAfter stirring the mixture at 70° C. for 2 h
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with water (2×20 mL) and brine (20 mL)
  4. dry with materialThen, the solution was dried (MgSO4)
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-fac1a290a49b462493c37b3f0b0cbc27
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08629138B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes