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

HRID 2300153
Notes
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Reaction equation

HRID 2300153 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 ethylacetate. 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 ethylacetate
  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-83c67eabe72f47259fa7a36af3a076b0
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06498159B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes