N-methyl-2-pyrrolidone → 6-Bromo-1-chloro-4-[(3-chloro-4-methoxybenzyl)amino]phthalazine

HRID 47317Notes

Reaction equation

HRID 47317 reaction equation
C1CCN2C(=NCCC2)CC1.[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([Cl:23])=[N:18][N:17]=[C:16]2Cl.Cl.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[CH2:30][NH2:31].CN1CCCC1=O>O>[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([Cl:23])=[N:18][N:17]=[C:16]2[NH:31][CH2:30][C:29]1[CH:32]=[CH:33][C:34]([O:35][CH3:36])=[C:27]([Cl:26])[CH:28]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27642873-Chloro-4-methoxybenzylamine hydrochlorideHCID 227444546-Bromo-1,4-dichlorophthalazine

Product 1

HCID 227444516-Bromo-1-chloro-4-[(3-chloro-4-methoxybenzyl)amino]phthalazineYield 31.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

5.2 ml DBU was added to a mixture of 3.8 g 6-bromo-1,4-dichlorophthalazine, 3.5 g 3-chloro-4-methoxybenzylamine hydrochloride and 30 ml 1-methyl-2-pyrrolidinone, and the mixture was stirred at 100° C. for 3 hr. After cooling, water was added to the reaction solution which was then extracted with ethyl acetate. The extract was washed with brine. It was dried over anhydrous magnesium sulfate and filtered, and the filtrate was evaporated. The resulting residue was purified by silica gel column chromatography to give 1.8 g of the title compound as a less polar compound.

Workup

  1. temperatureAfter cooling
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialIt was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a4aedde9338f494c9aa74bc4a25cae70
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Reaction notes

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