(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate → Methyl 4-formyl-3-nitrobenzoate

HRID 1782692Notes

Reaction equation

HRID 1782692 reaction equation
CN(C)/C=[CH:4]/[C:5]1[CH:10]=[CH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16].I([O-])(=O)(=O)=[O:20].[Na+]>O.O1CCCC1>[CH3:14][O:13][C:11]([C:8]1[CH:9]=[CH:10][C:5]([CH:4]=[O:20])=[C:6]([N+:15]([O-:17])=[O:16])[CH:7]=1)=[O:12]

Participants

4

Reactant 2

HCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoateHCID 23667635Sodium periodate

Product 1

HCID 3457222Methyl 4-formyl-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a mixture of 119.5 g (0.478 mol) of (E)-1-(dimethylamino)-2-[4-(methoxycarbonyl)-2-nitrophenyl]-ethene and 1.3 l of water/tetrahydrofuran mixture (1/1 v/v) were added, in batches, 308.0 g (1.44 mol) of sodium metaperiodate, whilst the reaction temperature was regulated at under +30° C. by external cooling with ice water. The mixture was stirred for a further 2.5 hours at room temperature and then filtered. The precipitate was thoroughly washed with ethyl acetate. The organic phase was separated off, the aqueous phase was thoroughly extracted with ethyl acetate. The combined ethyl acetate phases were dried over sodium sulphate and evaporated down in vacuo. The oil which crystallised after one day was further processed without any more purification. Yield: 87 g (87% of theory).

Workup

  1. customwas regulated at under +30° C.
  2. filtrationfiltered
  3. washThe precipitate was thoroughly washed with ethyl acetate
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was thoroughly extracted with ethyl acetate
  6. dry with materialThe combined ethyl acetate phases were dried over sodium sulphate
  7. customevaporated down in vacuo
  8. customThe oil which crystallised after one day
  9. customwas further processed without any more purification

Sources & evidence

ORD record
ord-8f43393d6a1145668204b71ffdc0ca52
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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