Dimethylformamide → HCID 59515876, compound

HRID 418472Notes

Reaction equation

HRID 418472 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[C:3]=1[N+:13]([O-:15])=[O:14].COC(OC)N(C)C.CN(C)C=O.C(OCC)(=O)C>>[Br:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:7])[O:8][CH:9]=[CH:12]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 59845702HCID 59845702, compound

Product 1

HCID 59515876HCID 59515876, compound

Conditions

Temperature
120 °C

Procedure

A pressure tube (150 mL) was charged with methyl 4-bromo-2-methyl-3-nitrobenzoate (2.1 g, 0.0077 mol), 1,1-dimethoxy-N,N-dimethylmethanamine (3.6 mL, 0.027 mol) and N,N-dimethylformamide (5 mL, 0.06 mol). The mixture was heated at 120° C. for 20 hours the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (100 mL, 1 mol). Silica Gel (20 g, 0.3 mol) was then added and the reaction was stirred at room temperature for 12 h. The reaction was filtered and the solvent was removed and the residue was purified by flash chromatography to afford the desired product. MS m/z=271.2 (M+H).

Workup

  1. customwas removed under reduced pressure
  2. additionSilica Gel (20 g, 0.3 mol) was then added
  3. filtrationThe reaction was filtered
  4. customthe solvent was removed
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4bcf9d0ffe914a77bbb8536f74803028
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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