Potassium Iodide → 6-Hydroxymethyl-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one

HRID 1714814Notes

Reaction equation

HRID 1714814 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[NH:8][C:7]=2[CH:13]=1.Cl[CH2:15][CH2:16][CH2:17][O:18][CH3:19].[F-].[K+].[I-].[K+]>C(#N)C>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[C:7]=2[CH:13]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 1189271-Chloro-3-methoxypropaneHCID 522689Potassium FluorideHCID 184524436-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 534011966-Hydroxymethyl-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1.79 g of 6-hydroxymethyl-4H-benzo[1,4]oxazin-3-one, 2.20 ml of 1-chloro-3-methoxypropane, 10 g of KF on aluminium oxide and 0.033 g of potassium iodid in 150 ml of acetonitrile is stirred under reflux for 72 hours. The reaction mixture is cooled and clarified by filtration, and the filltrate is evaporated to dryness. The title compound is obtained from the residue by flash chromatography (SiO2 60 F). Rf (CH2Cl2/MeOH 9:1)=0.60; Rt =2.74.

Workup

  1. temperatureunder reflux for 72 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationclarified by filtration
  4. customthe filltrate is evaporated to dryness

Sources & evidence

ORD record
ord-e0b029641a3642a4b651cdfd9aa6f3db
Source dataset
uspto-grants-2010_09
Patent number
US07799779B2

Reaction notes

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