Bromine → Diethyl 5-(bromoacetyl)-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

HRID 365087Notes

Reaction equation

HRID 365087 reaction equation
[Br:1]Br.[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10](=[O:22])[C:11]([C:19](=[O:21])[CH3:20])=[CH:12][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])[CH3:4]>Br>[Br:1][CH2:20][C:19]([C:11]1[C:10](=[O:22])[NH:9][C:8]([C:6]([O:5][CH2:3][CH3:4])=[O:7])=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=1)=[O:21]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 13752508Diethyl 5-acetyl-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Product 1

HCID 13752509Diethyl 5-(bromoacetyl)-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent2×

Procedure

Bromine (8.0 g, 0.050 mol) in 48% HBr is added dropwise to a stirred solution of diethyl-5-acetyl-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate (14.05 g, 0.05 mol) in 48% HBr (200 mL). Upon completion of this bromine addition the reaction mixture is poured onto ice (200 g) and the mixture is stirred until the ice has melted. Th crude product is collected by filtration and crystallized twice from an ethyl acetate-hexane mixture (1/2) affording diethyl 5-(bromoacetyl)-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate with mp 141°-142° C.

Workup

  1. additionis poured onto ice (200 g)
  2. filtrationTh crude product is collected by filtration
  3. customcrystallized twice from an ethyl acetate-hexane mixture (1/2)

Sources & evidence

ORD record
ord-bbc88d172dd84732912f22f583708974
Source dataset
uspto-grants-1986_08
Patent number
US04608079

Reaction notes

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