Triethylamine → 1-Chloro-4-((3-chloro-4-methoxybenzyl)amino)-6-phthalazinecarbonitrile

HRID 1595174Notes

Reaction equation

HRID 1595174 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([Cl:13])=[N:8][N:7]=[C:6]2Cl)#[N:2].[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:19][NH2:20].C(N(CC)CC)C>O1CCCC1>[Cl:13][C:9]1[C:10]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:12][CH:11]=2)[C:6]([NH:20][CH2:19][C:18]2[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:16]([Cl:15])[CH:17]=2)=[N:7][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7380383-Chloro-4-methoxybenzylamineHCID 106567381,4-Dichlorophthalazine-6-carbonitrile

Product 1

HCID 104510651-Chloro-4-((3-chloro-4-methoxybenzyl)amino)-6-phthalazinecarbonitrileYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

66.2 g of 6-cyano-1,4-dichlorophthalazine and 92 g of 3-chloro-4-methoxybenzylamine were suspended in 1,200 ml of tetrahydrofuran. After adding 250 ml of triethylamine, the resulting mixture was heated under reflux for 6 hours. The resulting crystals were filtered off and the filtrate was evaporated. The residue was purified by silica gel column chromatography (toluene:tetrahydrofuran=10:1) to give 59 g of 1-chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine as pale yellow crystals. M.p.: 213.0-214.5° C., Mass 359(MH+),

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 6 hours
  3. filtrationThe resulting crystals were filtered off
  4. customthe filtrate was evaporated
  5. customThe residue was purified by silica gel column chromatography (toluene:tetrahydrofuran=10:1)

Sources & evidence

ORD record
ord-62ae323658834ab08d0c501162fe7741
Source dataset
uspto-grants-2001_09
Patent number
US06288064B1

Reaction notes

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