6-Hydroxymethyl-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one → 4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde

HRID 1712602Notes

Reaction equation

HRID 1712602 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][CH2:15][O:16][CH3:17])[C:7]=2[CH:18]=1>[O-2].[O-2].[Mn+4].ClCCl>[CH3:17][O:16][CH2:15][CH2:14][CH2:13][N:8]1[C:7]2[CH:18]=[C:3]([CH:2]=[O:1])[CH:4]=[CH:5][C:6]=2[O:11][CH2:10][C:9]1=[O:12]

Participants

4

Reactant 1

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

Product 1

HCID 866100294-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

The solution of 6.08 g of 6-hydroxymethyl-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one and 300 ml of dichloromethane is admixed with 20.9 g of manganese dioxide and stirred over 8 hours. The reaction mixture is filtered and the filtrate is concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.59 (4:1 EtOAc-heptane); Rt=3.24.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-cb7d2c236d054010ab4a8fbb0a8b55cd
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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