Methyl 4-dimethylaminovinyl-3-nitrobenzoate → Methyl 4-formyl-3-nitrobenzoate

HRID 50363Notes

Reaction equation

HRID 50363 reaction equation
CN(C)C=[CH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16].I([O-])(=O)(=O)=[O:20].[Na+]>O1CCCC1.O.O.C(Cl)Cl>[CH:4]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])=[O:20]

Participants

6

Reactant 2

HCID 894336Methyl 4-dimethylaminovinyl-3-nitrobenzoateHCID 23667635Sodium periodate

Product 1

HCID 3457222Methyl 4-formyl-3-nitrobenzoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

1.2 g (4.8 mmol) of methyl 4-(2-dimethylaminovinyl)-3-nitrobenzoate were dissolved in 120 mL of tetrahydrofuran/water (1:1) and after the addition of 3.0 g (14.3 mmol) of sodium metaperiodate the mixture was stirred for 20 hours at ambient temperature. The suspension was then diluted with water and methylene chloride and extracted with methylene chloride. The combined organic extracts were washed with sodium hydrogen carbonate solution, dried, and evaporated down. The residue was chromatographed on silica gel and eluted with ethyl acetate/cyclohexane (1:3). Yield: 0.6 g (63% of theory); Rf value: 0.63 (silica gel, ethyl acetate/cyclohexane=1:1).

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts were washed with sodium hydrogen carbonate solution
  3. customdried
  4. customevaporated down
  5. customThe residue was chromatographed on silica gel
  6. washeluted with ethyl acetate/cyclohexane (1:3)

Sources & evidence

ORD record
ord-f6d982671ef64b3e8ae0bbc2d85e2e0b
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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