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Water → N-(6-(4-Nitrophenoxy)pyrimidin-4-yl)phenylamine

HRID 387990
Notes
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Reaction equation

HRID 387990 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C.O>CN1CCCC1=O.CCCCCC>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:7]=2)=[CH:10][CH:11]=1)([O-:17])=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 8857Ethyl Acetate2×HCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidine

Product 1

HCID 22936302N-(6-(4-Nitrophenoxy)pyrimidin-4-yl)phenylamineYield 82.5%

Reagents, catalysts & solvents 2

HCID 8058
Hexane
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-Chloro-6-(4-nitrophenoxy)pyrimidine (508 mg, 2.00 mmol) and aniline (559 mg, 6.00 mmol) were heated and stirred in 1-methylpyrrolidone (5 ml) at 90° C. for 3 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent-ethyl acetate:hexane=1:3), and the fraction containing the target substance was concentrated to obtain the title compound (508 mg, 1.65 mmol, 82%) as colorless crystals.

Workup

  1. washthe organic layer was washed with water and saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-a882d845f74f4f98bc25afba11330cb3
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372981B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes