1-Bromo-3-methoxypropane → HCID 19039704, compound

HRID 1684751Notes

Reaction equation

HRID 1684751 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:11]CCCOC)C.[CH2:18]([O:20][C:21](=O)[C:22]1C=CC=N[C:23]=1[OH:28])C.COCCCBr>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH3:18][O:20][CH2:21][CH2:22][CH2:23][O:28][N:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:4]([O:3][CH3:1])=[O:17])[C:6]1=[O:11]

Participants

6

Reactant 3

HCID 5245511-Bromo-3-methoxypropaneHCID 22377935HCID 22377935, compoundHCID 178468989HCID 178468989, compound

Product 1

HCID 19039704HCID 19039704, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

2-(3-Methoxypropoxy)-nicotinic acid ethyl ester: 2-Hydroxy-nicotinic acid ethyl ester (1.67 g), 3-methoxypropyl bromide (2.3 g) and silver carbonate (1.38 g) in toluene (80 ml) are reacted in accordance with the procedure described by Labaudiniere et al. (J. Med. Chem. 1992, 35, 4315-4324). Purification of the crude product by FC (dichloromethane-methanol-conc. ammonia 95:5:1) yields 1-(3-methoxypropoxy)-3-carbomethoxy-2(1H)-pyridinone (1.1 7 g), Rf (dichloromethane-methanol-conc. ammonia 95:5:1)=0.59, in the form of a pale-yellow oil, as well as the title compound (0.93 g), Rf (dichloromethane-methanol-conc. ammonia 95:5:1)=0.79, in the form of a yellowish oil.

Workup

  1. customPurification of the crude product by FC (dichloromethane-methanol-conc. ammonia 95:5:1)

Sources & evidence

ORD record
ord-75f83ac8ed794c6da1318082bea4c3fa
Source dataset
uspto-grants-1997_06
Patent number
US05641778

Reaction notes

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