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

HRID 2288500Notes

Reaction equation

HRID 2288500 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-nitro-benzoate 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-907adfc5a0384437b8045de1715c0610
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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