Pyridine → HCID 178481328, compound

HRID 2198545Notes

Reaction equation

HRID 2198545 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][N:13]([C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[C:19](=[O:28])[N:20]([CH3:27])[C:21]2=[O:26])[C:14](Cl)=[O:15].N1C=CC=CC=1>C(#N)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][NH:11][C:14]([N:13]([CH3:12])[C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[C:19](=[O:28])[N:20]([CH3:27])[C:21]3=[O:26])=[O:15])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1170503-(N-Methyl-N-chlorocarbonylamino)-N-methylphthalimideHCID 3310889(4-Nitrophenyl)hydrazine

Product 1

HCID 178481328HCID 178481328, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

p-Nitrophenylhydrazine (1.5 g, 10 mmole), N-methyl-N-(2-methyl-1,3-dioxoisoindolin-4-yl) carbamoyl chloride (2.5 g, 10 mmole) and 2 ml pyridine were combined in 25 ml dry acetonitrile, heated to reflux, then stirred at room temperature for 4 hours. The solid formed was collected and washed with ether to give 2.6 g of product, m.p. 194°-196° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customThe solid formed
  4. customwas collected
  5. washwashed with ether

Sources & evidence

ORD record
ord-1428b4315c51438fa32572add6c41c47
Source dataset
uspto-grants-1982_11
Patent number
US04358525

Reaction notes

Loading…