Sodium ethoxide → 4-(3-(2-oxopyrrolidin-1-yl)benzyl)phthalazin-1(2H)-one

HRID 459749Notes

Reaction equation

HRID 459749 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[NH:17][N:16]=2)[CH:9]=1)=[O:6].[O-]CC.[Na+]>C(O)C>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][N:7]1[C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:25])[NH:17][N:16]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 184443774-chloro-N-[3-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]butyramide

Product 1

HCID 184443704-(3-(2-oxopyrrolidin-1-yl)benzyl)phthalazin-1(2H)-oneYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-N-[3-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]butyramide (1 g, 2.8 mmol) was added in portions at 0° C. to a stirred solution of sodium ethoxide [from sodium (0.15 g, 6.7 mmol)] in ethanol (10 ml), then the mixture was heated under reflux for 3 hours, cooled to ambient temperature and added to ice-water (50 ml). The resulting solid was collected by filtration, washed with water (10 ml) and dried in vacuo to give 4-[3-(2-oxopyrrolidin-1-yl)benzyl]-2H-phthalazin-1-one (0.77 g) as an off-white solid, m.pt. 206–207° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 2.00 (m, 2H) (—CH2CH2CH2—), 2.55 (m-partially obscured by DMSO peak, 2H) (—NCH2—), 3.75 (t, 2H) (—COCH2—), 4.3 (s, 2H) (ArCH2—), 7.05 (d, 1H) (ArH), 7.25 (t, 1H) (ArH), 7.5 (d, 1H) (ArH), 7.7 (s, 1H) (ArH), 7.75–8.0 (m, 3H) (3×ArH), 8.25 (d, 1H) (ArH); m/z (M+H)+. 320, 100% purity.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water (10 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-5a0fb371df9d4c8896db1ff6f5fa5a84
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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