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

HRID 387691Notes

Reaction equation

HRID 387691 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.O.C(=O)(O)O>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 21993411Carbonic acid--water (1/1)HCID 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 bicarbonate 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 Silicia 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-c6a896a0302543df9d2f93bca11e601d
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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