Hexane → HCID 10662594, compound

HRID 479593Notes

Reaction equation

HRID 479593 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:15][CH2:16][C:17]([NH2:19])=[O:18])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:21][C:22](=O)[CH2:23][CH3:24].C(=O)([O-])O.[Na+].CCCCCC>CC(CC)=O>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([CH:21]=[C:22]([CH2:23][CH3:24])[C:15]=2[CH2:16][C:17]([NH2:19])=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 131561-Bromo-2-butanoneHCID 516892Sodium BicarbonateHCID 10611091HCID 10611091, compound

Product 1

HCID 10662594HCID 10662594, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of the pyridine derivative (16, 4.00 g, 15.6 m mol), 1-bromo-2-butanone (3.53 g, 23.4 m mol) and sodium hydrogencarbonate (6.55 g, 78 m mol) in methylethylketone (30 ml) was heated under reflux for 60 hours. The solid was filtered off. The volatile materials were removed by distillation under reduced pressure. The residue was chromatographed on silica gel eluting with hexane:ethyl acetate (1:2) and with ethyl acetate. The first fraction was crystallized from benzene:hexane to give 2.32 g (48.2% yield) of the titled compound 17b and, mp, 117-119° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 60 hours
  3. filtrationThe solid was filtered off
  4. customThe volatile materials were removed by distillation under reduced pressure
  5. customThe residue was chromatographed on silica gel eluting with hexane:ethyl acetate (1:2) and with ethyl acetate
  6. customThe first fraction was crystallized from benzene

Sources & evidence

ORD record
ord-4b2a20c6508c41f5a6cd96a8b52f6053
Source dataset
uspto-grants-2003_11
Patent number
US06645976B1

Reaction notes

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