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

HRID 1161186Notes

Reaction equation

HRID 1161186 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].COC(OC)N(C)C.CN(C)C=O>>[N+:12]([C:11]1[CH:10]=[CH:9][CH:8]=[C:3]2[C:2]=1[CH:1]=[CH:7][O:6][C:4]2=[O:5])([O-:14])=[O:13]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 601165Methyl 2-methyl-3-nitrobenzoate

Product 1

HCID 100127605-nitro-1H-isochromen-1-oneYield 94.2%

Conditions

Temperature
115 °C

Procedure

Methyl 2-methyl-3-nitrobenzoate (5 g, 0.02 mol) and 1,1-dimethoxy-N,N-dimethylmethanamine (10 mL, 0.07 mol) were dissolved in N,N-dimethylformamide (30 mL, 0.4 mol). The mixture was stirred at 115° C. for 17 hours. The volatiles were removed on a rotavapor. The residue was dissolved in ethylacetate (400 mL) and then silica gel (400 g) was added. The mixture was stirred at room temperature for 3 hours. Filtered, rinsed with ethylacetate (400 mL×3). Combined filtrates were concentrated to dryness to get a brown solid (3.6 g). MS m/z=192.0 (M+1).

Workup

  1. customThe volatiles were removed on a rotavapor
  2. dissolutionThe residue was dissolved in ethylacetate (400 mL)
  3. additionsilica gel (400 g) was added
  4. stirringThe mixture was stirred at room temperature for 3 hours
  5. filtrationFiltered
  6. washrinsed with ethylacetate (400 mL×3)
  7. concentrationCombined filtrates were concentrated to dryness

Sources & evidence

ORD record
ord-47d681e0419a4ff79cf01d27f45a1f59
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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