Dimethylformamide dimethyl acetal → 5-nitro-1H-isochromen-1-one

HRID 420614Notes

Reaction equation

HRID 420614 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH3:13].COC(OC)N(C)C>CN(C)C=O>[N+:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]2[C:5]=1[CH:13]=[CH:1][O:2][C:3]2=[O:14])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 601165Methyl 2-methyl-3-nitrobenzoate

Product 1

HCID 100127605-nitro-1H-isochromen-1-oneYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.4 g (84.03 mmol) of 2-methyl-3-nitrobenzoic acid methyl ester is stirred with 26.8 g (225.1 mmol) of N,N-dimethylformamide dimethylacetal in 85 ml of dimethylformamide for 12 hours at 130° C. The solvent is drawn off in a rotary evaporator, the residue is taken up in methyl-tert-butyl ether and washed three times with water. After washing with saturated NaCl solution, the organic phase is dried. After the desiccant is filtered off and the solvent is spun off, the remaining residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 8.73 g (54.4%) of the desired compound is isolated.

Workup

  1. customThe solvent is drawn off in a rotary evaporator
  2. washwashed three times with water
  3. washAfter washing with saturated NaCl solution
  4. customthe organic phase is dried
  5. filtrationAfter the desiccant is filtered off
  6. customthe remaining residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4eddb5107f3243b79357172874a7d77f
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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