Water → 7-Benzyloxy-3-nitroquinoline

HRID 1938352Notes

Reaction equation

HRID 1938352 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([OH:14])[CH:8]=2)([O-:3])=[O:2].[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C>[CH2:17]([O:14][C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[N:6]2)=[CH:11][CH:10]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1357342933-Nitroquinolin-7-ol

Product 1

HCID 214693237-Benzyloxy-3-nitroquinolineYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (75 mL) was dissolved 3-nitro-7-hydroxyquinoline (5.0 g, 26.2 mmol.). Under chilling with ice, to the solution was added sodium hydride (1.15 g, 29 mmol.). After 20 minutes, benzyl bromide (3.4 mL, 29 mmol.) was further added for 10 minutes. The mixture was then stirred overnight at room temperature. After the completion of reaction was confirmed, the mixture was poured into a mixture of ice and water. The precipitated crystalline product was collected by filtration, washed with water, and dried, to give the desired compound (7 g) as a white crystalline product (yield 95%).

Workup

  1. temperatureUnder chilling with ice, to the solution
  2. customAfter the completion of reaction
  3. filtrationThe precipitated crystalline product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ca770e18073f4ee7a9dbe7f33b847497
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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