Water → 3-[[3-(4-Methoxyphenyl)-1,2,4-triazolo[3,4-a]phthalazin-6-yl]oxy]-2-pyrrolidinone

HRID 2232236Notes

Reaction equation

HRID 2232236 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2=[N:12][N:13]=[C:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:4]2[N:3]=1.[H-].[Na+].Br[CH:26]1[CH2:30][CH2:29][NH:28][C:27]1=[O:31].O>CN(C)C=O>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[N:4]3[N:3]=[C:2]([O:1][CH:26]4[CH2:30][CH2:29][NH:28][C:27]4=[O:31])[C:11]4[C:6]([C:5]3=[N:12][N:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=4)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 101034713-Bromopyrrolidin-2-oneHCID 178489106HCID 178489106, compound

Product 1

HCID 212833373-[[3-(4-Methoxyphenyl)-1,2,4-triazolo[3,4-a]phthalazin-6-yl]oxy]-2-pyrrolidinoneYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Hydroxy-3-(4-methoxyphenyl)-1,2,4-triazolo[3,4-a]phthalazine, (9.8 g), is suspended in N,N-dimethylformamide (100 ml) and added of 50% sodium hydride in mineral oil (1.7 g). The mixture is heated to 50°-60° C. and stirred for about 2 hours. After cooling to room temperature the mixture is added portionwise with 3-bromo-2-pyrrolidone (5.5 g). [This product is prepared according to F. Korte, H. Wanholf, Ber. 97, 1976 (1964)]. Then stirring is continued for about 5 hours at a temperature of about 70° C. The mixture is then cooled to room temperature and poured into water (800 ml). The residue, which is collected by filtration, is then crystallized from ethanol/chloroform. (Yield=82%). M.p. 290°-293° C.

Workup

  1. temperatureThe mixture is heated to 50°-60° C.
  2. custom[This product is prepared
  3. stirringThen stirring
  4. waitis continued for about 5 hours at a temperature of about 70° C
  5. temperatureThe mixture is then cooled to room temperature
  6. filtrationThe residue, which is collected by filtration
  7. customis then crystallized from ethanol/chloroform

Sources & evidence

ORD record
ord-ef3962880fda4ae38f769bfeea5a2600
Source dataset
uspto-grants-1988_11
Patent number
US04788186

Reaction notes

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