Methyl morpholine oxide → 2-Methyl-5-nitro-4-oxo-4H-1-benzopyran-8-carbaldehyde

HRID 557427Notes

Reaction equation

HRID 557427 reaction equation
Br[CH:2](Br)[C:3]1[CH:4]=[CH:5][C:6]([N+:15]([O-:17])=[O:16])=[C:7]2[C:12]=1[O:11][C:10]([CH3:13])=[CH:9][C:8]2=[O:14].C[N+]1([O-])CC[O:23]CC1>C(#N)C>[CH3:13][C:10]1[O:11][C:12]2[C:7]([C:8](=[O:14])[CH:9]=1)=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=2[CH:2]=[O:23]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 578286378-(Dibromomethyl)-2-methyl-5-nitro-4H-1-benzopyran-4-one

Product 1

HCID 578286522-Methyl-5-nitro-4-oxo-4H-1-benzopyran-8-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

175 mg (0.47 mmol) of 8-(dibromomethyl)-2-methyl-5-nitro-4H-chromen-4-one are heated under reflux with 151 mg (1.29 mmol) of N-methylmorpholine N-oxide with the addition of molecular sieves in 15 ml of acetonitrile overnight. After filtration through kieselguhr, the solvent is removed in vacuo, and the residue is purified by preparative HPLC. 23 mg (24% of theory) of the title compound are obtained.

Workup

  1. filtrationAfter filtration through kieselguhr
  2. customthe solvent is removed in vacuo
  3. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-94997dea25a14cd89bbdf53f3e0bc59d
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

Loading…