Dimethylformamide → HCID 59515876, compound

HRID 1161181Notes

Reaction equation

HRID 1161181 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) and heated at 120° C. for 20 hours. The reaction gave multiple products. The solvent was removed 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 stirred at room temperature for 12 h. The reaction was filtered and the solvent removed and the residue purified by flash chromatography. MS m/z=271.2 (M+H).

Workup

  1. customThe reaction gave multiple products
  2. customThe solvent was removed
  3. additionSilica Gel (20 g, 0.3 mol) was then added
  4. filtrationThe reaction was filtered
  5. customthe solvent removed
  6. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-697111509fe240468d17033abfafd7e1
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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