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

HRID 1906102Notes

Reaction equation

HRID 1906102 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. The 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. filtrationThe crude product is collected by filtration
  3. customcrystallized twice from an ethyl acetate-hexane mixture (1/2)

Sources & evidence

ORD record
ord-73fd62814263411195bf7e324cc6c1f9
Source dataset
uspto-grants-1987_03
Patent number
US04650514

Reaction notes

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