(E)-Methyl 2-(2-(dimethylamino)vinyl)-3-nitrobenzoate → 5-nitro-1H-isochromen-1-one

HRID 749213Notes

Reaction equation

HRID 749213 reaction equation
CN(C)/C=[CH:4]/[C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]>CCOC(C)=O>[N+:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:6]2[C:5]=1[CH:4]=[CH:10][O:9][C:7]2=[O:8])([O-:17])=[O:16]

Participants

3

Reactant 1

HCID 12148522(E)-Methyl 2-(2-(dimethylamino)vinyl)-3-nitrobenzoate

Product 1

HCID 100127605-nitro-1H-isochromen-1-oneYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(E)-Methyl 2-(2-(dimethylamino)vinyl)-3-nitrobenzoate was re-dissolved in EtOAc (200 mL), and silica gel (200 g) was added. The resulting suspension was stirred at room temperature for 1 h. The EtOAc solution was filtered off. Silica gel was washed with EtOAc (2×150 mL) and the combined organics were evaporated and dried under reduced pressure to yield 5-nitro-1H-isochromen-1-one (4.0 g, 21.0 mmol, 82% after two steps) as a brown solid.

Workup

  1. additionsilica gel (200 g) was added
  2. filtrationThe EtOAc solution was filtered off
  3. washSilica gel was washed with EtOAc (2×150 mL)
  4. customthe combined organics were evaporated
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-cebd356b32e3458ab09d2a10f3374721
Source dataset
uspto-grants-2008_07
Patent number
US07402596B2

Reaction notes

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