4-Nitrophenol → 7-Benzyloxy-6-cyano-4-(4-nitrophenoxy)quinoline

HRID 1010075Notes

Reaction equation

HRID 1010075 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:20]#[N:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)([O-:24])=[O:23].N1C(C)=CC=CC=1C.[Na]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:31][C:28]3[CH:29]=[CH:30][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:20]#[N:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 79372,6-LutidineHCID 5360545SodiumHCID 226465197-Benzyloxy-4-chloro-6-cyanoquinoline

Product 1

HCID 229365907-Benzyloxy-6-cyano-4-(4-nitrophenoxy)quinolineYield 52.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
156.5 °C

Procedure

To the 7-benzyloxy-4-chloro-6-cyanoquinoline (2.60 g, 8.83 mmol) described in WO98/13350 there were added 4-nitrophenol (2.46 g, 17.7 mmol) and lutidine (2.06 ml, 17.7 mmol), and the mixture was heated and stirred at 155-158° C. for 2 hours. After returning the reaction system to room temperature, it was dissolved in tetrahydrofuran, saturated sodium bicarnobate water was added and stirred therewith for 10 minutes, the mixture was concentrated under reduced pressure, the precipitated solid was filtered out and subjected to silica gel column chromatography (Fuji Silysia NH Type, eluent—hexane:ethyl acetate=50:50→ethyl acetate alone), the fraction containing the target substance was concentrated and the obtained solid was washed with diethyl ether. It was then dried under reduced pressure to obtain the title compound (1.84 g, 4.63 mmol, 52.6%).

Workup

  1. temperaturethe mixture was heated
  2. customto room temperature
  3. stirringstirred
  4. waitfor 10 minutes
  5. concentrationthe mixture was concentrated under reduced pressure
  6. filtrationthe precipitated solid was filtered out
  7. additionethyl acetate=50:50→ethyl acetate alone), the fraction containing the target substance
  8. concentrationwas concentrated
  9. washthe obtained solid was washed with diethyl ether
  10. customIt was then dried under reduced pressure

Sources & evidence

ORD record
ord-42c1303033b74d8e9370fae8f5496fcd
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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