Pyridinium chloride → HCID 21293345, compound

HRID 622133Notes

Reaction equation

HRID 622133 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17](=[O:21])[N:16]([CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[N:15]=[CH:14]3)=[CH:5][CH:4]=1.[ClH:28].N1C=CC=CC=1>O>[ClH:28].[OH:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17](=[O:21])[N:16]([CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[N:15]=[CH:14]3)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13827282HCID 13827282, compound

Product 1

HCID 21293345HCID 21293345, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

Trans-6-[2-(4-Methoxyphenyl)ethenyl]-2-[3-(dimethylamino)propyl]-phthalazin-1(2H)-one (prepared as in Example XIV) (46.6 gm, 0.122 mole) and 245 gm pyridine hydrochloride were heated together with stirring at 180° C. for 7 hours. The hot melt was added to 1200 ml water and stirred over night. The product was filtered off and washed with three 400 ml portions of water. The damp product was slurried in 350 ml of tetrahydrofuran plus 350 ml methanol, acidified with gaseous HCl, filtered and washed with ethanol. The product, which weighed 36 gm, was recrystallized from 275 ml water. Wgt=30.2 gm, mp=283°-283° C.

Workup

  1. stirringstirred over night
  2. filtrationThe product was filtered off
  3. washwashed with three 400 ml portions of water
  4. filtrationfiltered
  5. washwashed with ethanol
  6. customwas recrystallized from 275 ml water

Sources & evidence

ORD record
ord-97f10983055c4d01ae96411f2ebfc09d
Source dataset
uspto-grants-1988_09
Patent number
US04769369

Reaction notes

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