O-Toluidine → HCID 18917470, compound

HRID 1735251Notes

Reaction equation

HRID 1735251 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[NH2:24][C:25]1[C:26]([CH3:31])=[CH:27][CH:28]=[CH:29][CH:30]=1>CN(C)C=O>[CH3:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:24][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 2194772510-[(6-Chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 18917470HCID 18917470, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g of 10-[(6-chloro-3-pyridinyl)carbonyl]-10, 11-dihydro-5H-pyrrolo[2,1-c][1, 4]-benzodiazepine and 0.36 g of o-toluidine in 60 ml of N,N-dimethylformamide is refluxed for 16 hours. The mixture is poured into 200 ml of ice-water and extracted with three 100 ml portions of chloroform. The extract is washed with water, dried (Na2SO4) and the solvent removed. The residue is purified by chromatography on silica gel prep-plates with hexane-ethyl acetate (5:1) as solvent to give 0.56 g of yellow solid: mass spectrum (CI) 395.2 (M+H).

Workup

  1. temperatureis refluxed for 16 hours
  2. extractionextracted with three 100 ml portions of chloroform
  3. washThe extract is washed with water
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed
  6. customThe residue is purified by chromatography on silica gel prep-plates with hexane-ethyl acetate (5:1) as solvent

Sources & evidence

ORD record
ord-2fc3096ca00e469190812a4faf01ab6a
Source dataset
uspto-grants-1996_07
Patent number
US05536718

Reaction notes

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