Chlorobenzene → 5-Methyl-6-[2-(4-pyridyl)-5-benzimidazolyl]-4,5-dihydropyridazin-3-one

HRID 1494313Notes

Reaction equation

HRID 1494313 reaction equation
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:10][CH:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([NH2:24])[CH:18]=2)=[N:15][NH:14][C:13](=[O:25])[CH2:12]1.ClC1C=CC=CC=1>C(O)(=O)C>[CH3:10][CH:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]3[N:23]=[C:1]([C:2]4[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=4)[NH:24][C:19]=3[CH:18]=2)=[N:15][NH:14][C:13](=[O:25])[CH2:12]1

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 417436Pyridine-4-carbonyl chlorideHCID 34410526-(3,4-Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 137152275-Methyl-6-[2-(4-pyridyl)-5-benzimidazolyl]-4,5-dihydropyridazin-3-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 17 g of isonicotinoyl chloride, 21.8 g of 5-methyl-6-(3,4-diaminophenyl)-4,5-dihydropyridazin-3-one ("IIa"; m.p. 195°-196°) and 400 ml of chlorobenzene is boiled for 2 hours. After having been cooled, the usual working up is carried out and, initially, an oily mixture of 5-methyl-6-(3-amino-4-isonicotinamidophenyl)- and 5-methyl-6-(3-isonicotinamido-4-aminophenyl)-4,5-dihydropyridazin-3-one is obtained, which is dissolved in 400 ml of acetic acid and boiled for 3 hours. After having been cooled, 5-methyl-6-[2-(4-pyridyl)-5-benzimidazolyl]-4,5-dihydropyridazin-3-one ("M"), dihydrate, m.p. 195°-198° (decomposition) is obtained. Dihydrochloride-dihydrate, m.p. 224°-227°. Methanesulphonate, m.p. 282°-285°.

Workup

  1. temperatureAfter having been cooled
  2. customis obtained
  3. waitboiled for 3 hours
  4. temperatureAfter having been cooled

Sources & evidence

ORD record
ord-d05f4471791a420d8079248da5a4b752
Source dataset
uspto-grants-1991_06
Patent number
US05026705

Reaction notes

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