Dimethylformamide → HCID 13827286, compound

HRID 978657Notes

Reaction equation

HRID 978657 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]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:15]=[CH:14]3)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1.CN(C=O)C>O>[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]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:15]=[CH:14]3)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10176127Pyridinium chlorideHCID 13827285HCID 13827285, compound

Product 1

HCID 13827286HCID 13827286, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

Trans-6-[2-(4-methoxyphenyl)ethenyl]-2-(2-pyridyl)-1(2H)-phthalazinone (7 g) and pyridine hydrochloride were thoroughtly mixed and heated to 180° C. for 21/2 hours. The solution was cooled to about 120° C.; then DMF (30 ml) was added followed by water (80 ml). The mixture was cooled to 20° C., filtered and the precipitate was washed with isopropanol. The solid mass was recrystallized from DMF to give 3.7 g of the phenol, mp=272° C.

Workup

  1. temperatureThe solution was cooled to about 120° C.
  2. temperatureThe mixture was cooled to 20° C.
  3. filtrationfiltered
  4. washthe precipitate was washed with isopropanol
  5. customThe solid mass was recrystallized from DMF

Sources & evidence

ORD record
ord-827127a114ce46f287fb8ee4a942824b
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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