HCID 13827271, compound → HCID 13827272, compound

HRID 978646Notes

Reaction equation

HRID 978646 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[NH:15][N:14]=[CH:13]3)=[CH:4][CH:3]=1>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]\[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[NH:15][N:14]=[CH:13]3)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 13827271HCID 13827271, compound

Product 1

HCID 13827272HCID 13827272, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
45 °C

Procedure

Trans-6-[2-(4-Hydroxyphenyl)ethenyl]-1(2H)-phthalazinone (12.4 gm) (produced in Example 2) was dissolved in 415 ml DMF by warming to 45° C. The solution was cooled back to 20° C. and diluted with an additional 200 ml DMF. The slightly cloudy solution was clarified by filtration, and the clear solution was irradiated in a soft glass container with 254 nm ultraviolet light for about 24 hours. The resulting solution was added with stirring to 6 L. water and allowed to settle for about 2 hours. The supernatant fluid, was decanted and the solid residue was filtered and washed with water and dried. Wt=7.4 gm, >95% cis by HPLC. mp=210°-22-° C (d).

Workup

  1. temperatureThe solution was cooled back to 20° C.
  2. filtrationThe slightly cloudy solution was clarified by filtration
  3. customthe clear solution was irradiated in a soft glass container with 254 nm ultraviolet light for about 24 hours
  4. additionThe resulting solution was added
  5. customThe supernatant fluid, was decanted
  6. filtrationthe solid residue was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-67a963b702764e5184e9a997dfaa5695
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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