3-(Chloromethyl)pyridine → HCID 20097008, compound

HRID 1769599Notes

Reaction equation

HRID 1769599 reaction equation
[OH:1][C:2]1[C:3]2[C:4](=[N:8][O:9][N+:10]=2[O-:11])[N:5]=[CH:6][N:7]=1.[H-].[Li+].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][Cl:21])[CH:15]=1>C1COCC1.CN(C=O)C>[ClH:21].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:7]2[C:2](=[O:1])[C:3]3=[N+:10]([O-:11])[O:9][N:8]=[C:4]3[N:5]=[CH:6]2)[CH:15]=1

Participants

6

Reactant 3

HCID 183583-(Chloromethyl)pyridineHCID 62714Lithium hydrideHCID 178526302HCID 178526302, compound

Product 1

HCID 20097008HCID 20097008, compoundYield 10.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

5.0 g (33 mmol) of 7-hydroxy-[1,2,5]oxadiazolo[3,4-d]pyrimidine-1-oxide and 0.3 g (38 mmol) of lithium hydride are heated at 50° C. for 30 min in 70 ml of THF. After addition of a solution of 5.9 g (46 mmol) of 3-picolyl chloride in 30 ml of DMF, the mixture is heated at 60° C. for 2 h. The solvents are stripped off completely in a rotary evaporator, and the residue is digested several times with THF. The product is precipitated from the combined THF extracts by addition of ethereal hydrochloric acid and recrystallised from methanol. 1 g of 6-(3-picolyl)-[1,2,5]oxadiazolo[3,4-d]pyrimidine-7(6H)-one-1-oxide hydrochloride is obtained.

Workup

  1. customThe solvents are stripped off completely in a rotary evaporator
  2. customThe product is precipitated from the combined THF
  3. additionextracts by addition of ethereal hydrochloric acid
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-2bf6511eaee9403889d6a01c3cc5b14d
Source dataset
uspto-grants-1995_01
Patent number
US05382585

Reaction notes

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