Acetic Acid → 3-Methyl-1-[3-(4oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]pyrrole-2,5-dione

HRID 459750Notes

Reaction equation

HRID 459750 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][N:7]=1.[CH3:20][C:21]1[C:22](=[O:27])[O:23][C:24](=O)[CH:25]=1.C(O)(=O)C>O>[CH3:20][C:21]1[C:22](=[O:27])[N:1]([C:2]2[CH:19]=[CH:18][CH:17]=[C:4]([CH2:5][C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9](=[O:16])[NH:8][N:7]=3)[CH:3]=2)[C:24](=[O:23])[CH:25]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12012Citraconic AnhydridesHCID 184443754-(3-aminobenzyl)-2H-phthalazin-1-one

Product 1

HCID 184443653-Methyl-1-[3-(4oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 4-(3-aminobenzyl)-2H-phthalazin-1-one (0.1 g, 0.4 mmol; prepared in a manner similar to that described in Example 1), 3-methylfuran-2,5-dione (0.045 g, 0.4 mmol) and acetic acid (4 ml) was heated under reflux for 8.25 hours and allowed to stand at ambient temperature for 65 hours, then it was diluted with water (10 ml). The resulting solid was collected by filtration, washed with water (10 ml) and dried in vacuo to give 3-methyl-1-[3-(4oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]pyrrole-2,5-dione (0.068 g) as an off-white solid, 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 1.95 (s, 3H) (CH3), 4.3 (s, 2H) (ArCH2—), 6.7 (s, 1H) (—COCH═CMeCO—), 7.15 (d, 1H) (ArH), 7.2 (s, 1H) (ArH), 7.25–7.35 (m, 2H) (2×ArH), 7.7–7.9 (m, 3H) (3×ArH), 8.2 (d, 1H) (ArH), 12.55 (s, 1H) (CONH); m/z (M+H)+. 346, 100% purity.

Workup

  1. customprepared in a manner similar to
  2. temperaturewas heated
  3. temperatureunder reflux for 8.25 hours
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water (10 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-64c25e696790410fba472dec4b56e5c1
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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