Pyridine → HCID 58533481, compound

HRID 2273986Notes

Reaction equation

HRID 2273986 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[OH:24].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O1CCOCC1>[F:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[O:24][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 98252-Fluoro-4-nitrophenolHCID 106078294-Chloro-7-methoxyquinoline

Product 1

HCID 58533481HCID 58533481, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To 4-chloro-7-methoxyquinoline (0.900 g, 4.6 mmol), 2-fluoro-4-nitrophenol (2.3 g, 14 mmol), and N,N-dimethylpyridin-4-amine (0.068 g, 0.56 mmol) was added dioxane (10 mL) and pyridine (6.4 ml, 79 mmol). The resulting mixture was heated at 110° C. in an argon-purged sealed tube for 16 hours. An aliquot was analyzed by LCMS and indicated the presence of desired product. The reaction mixture was concentrated in vacuo and diluted with 2 N NaOH. The resulting solid was filtered, and the filtrate was extracted with CH2Cl2. The organic layers were dried over sodium sulfate and filtered through a pad of silica gel along with the solids using 10% MeOH/CH2Cl2 as eluent. The collected fractions were concentrated in vacuo to yield 4-(2-fluoro-4-nitrophenoxy)-7-methoxyquinoline (0.900 g, 2.3 mmol, 49% yield) as a brownish solid. Calcd for C16H11FN2O4: [M]+=314. Found: [M+H]+=315.

Workup

  1. custompurged
  2. customsealed tube for 16 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with 2 N NaOH
  5. filtrationThe resulting solid was filtered
  6. extractionthe filtrate was extracted with CH2Cl2
  7. dry with materialThe organic layers were dried over sodium sulfate
  8. filtrationfiltered through a pad of silica gel along with the solids
  9. concentrationThe collected fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-771567c8d8e54282bcc5ba97887180f1
Source dataset
uspto-grants-2015_09
Patent number
US09126935B2

Reaction notes

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