Benzoyl chloride → N-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzamide

HRID 497035Notes

Reaction equation

HRID 497035 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[NH:13][N:12]=1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[O:21]=[C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]([CH2:10][NH:9][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:12][NH:13]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 168196334-(Aminomethyl)-1,2-dihydrophthalazin-1-one hydrochloride

Product 1

HCID 7185872N-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (5.9 ml, 42 mmol) was added dropwise to a stirred suspension of 4-aminomethyl-2H-phthalazin-1-one hydrochloride (Geterotsikl. Soedin, 1972, (9), 15) (3.00 g, 14.2 mmol) in DMF (150 ml) at room temperature under nitrogen. The mixture was stirred for 1.5 h before the addition of benzoyl chloride (2.5 ml, 22 mmol) and then stirred at room temperature overnight. The reaction mixture was filtered and water added to the filtrate to form a solid. The mixture was cooled and the solid collected by filtration, washed successively with diethyl ether and isohexane, and dried in vacuo to give the title-compound (3.18 g, 80%), 1H NMR (360 MHZ, d6-DMSO) δ 4.81 (2H, d, J=5.6 Hz, CH2), 7.43-7.53 (3H, m, 3 of Ar—H), 7.83-7.96 (4H, m, 4 of Ar—H), 8.08 (1H, d, J=7.9 Hz, Ar—H), 8.28 (1H, dd, J=7.8 and 1.2 Hz, Ar—H), 8.98 (1H, br s, NH), 12.62 (1H, s NH).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionwater added to the filtrate
  3. customto form a solid
  4. temperatureThe mixture was cooled
  5. filtrationthe solid collected by filtration
  6. washwashed successively with diethyl ether and isohexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e0da50ea729240e0a3387bdae40b878a
Source dataset
uspto-grants-2005_09
Patent number
US06949549B2

Reaction notes

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