Pyridine → HCID 67045214, compound

HRID 1023688Notes

Reaction equation

HRID 1023688 reaction equation
CO[C:3](=[O:15])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13]Br.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=CC=CC=1>C(O)C>[N+:10]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:3](=[O:15])[N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13]2)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoate

Product 1

HCID 67045214HCID 67045214, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromomethyl-6-nitro-benzoic acid methyl ester (0.40 g, 1.46 mmol) and aniline (0.23 g, 2.44 mmol) in ethanol (20 ml) was added with pyridine (0.15 g, 1.95 mmol), and the mixture was refluxed by heating for 30 hours. The reaction solution was cooled to room temperature, and then poured into ice water, and the deposited crystals were collected by filtration, washed with ethanol and water, and dried. The resulting crystals were recrystallized (acetone) to obtain 7-nitro-2-phenyl-2,3-dihydro-isoindol-1-one as pale yellow crystals (0.23 g, yield: 62.9%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 30 hours
  3. filtrationthe deposited crystals were collected by filtration
  4. washwashed with ethanol and water
  5. customdried
  6. customThe resulting crystals were recrystallized (acetone)

Sources & evidence

ORD record
ord-da36eabc99cc4f2cac86f64d0ff550a0
Source dataset
uspto-grants-2014_05
Patent number
US08722723B2

Reaction notes

Loading…