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

HRID 1699235Notes

Reaction equation

HRID 1699235 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-e87b5e34244d42d5b02e4a9c989a01de
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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