Dimethylformamide dimethyl acetal → HCID 86621577, compound

HRID 420166Notes

Reaction equation

HRID 420166 reaction equation
N([CH:4](OC)[O:5]C)(C)C.[CH3:9][C:10]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][C:11]=1[O:24][CH3:25]>CC(N(C)C)=O.C(Cl)(Cl)Cl>[CH3:25][O:24][C:11]1[CH:12]=[C:13]([CH:19]=[C:20]([N+:21]([O-:23])=[O:22])[C:10]=1[CH2:9][CH:4]=[O:5])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 66649426HCID 66649426, compound

Product 1

HCID 86621577HCID 86621577, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

13.3 ml of Me2NCH(OMe)2 was added to a solution of 4.78 g of ethyl 4-methyl-3-(methoxy)-5-nitrobenzoate in 10 ml of dimethylacetamide and the mixture was heated at 80° C. in a sealed tube for 40 minutes. The mixture was diluted with CHCl3, washed with water, dried over Na2SO4, and concentrated. The residue was purified on SiO2 column chromatography to give 4.02 g of the intended compound as a pale tan solid.

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified on SiO2 column chromatography

Sources & evidence

ORD record
ord-bf4ba332d60443b58759580e755e4dc7
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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