Nitric Acid → HCID 178526775, compound

HRID 598380Notes

Reaction equation

HRID 598380 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[C:12]2[OH:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:20]([O-])([OH:22])=[O:21]>C(O)(=O)CC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([N+:20]([O-:22])=[O:21])=[C:12]2[OH:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178516436HCID 178516436, compound

Product 1

HCID 178526775HCID 178526775, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-benzyloxyquinolin-4-ol (65.7 g) and propionic acid (660 mL) was heated at 110° C. with vigorous stirring. Nitric acid (19.2 mL of 16 M) was slowly added over a period of 30 minutes while maintaining the reaction temperature below 120° C. After the addition, the reaction was allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed sequentially with propionic acid, isopropanol, and diethyl ether. The material was dried in a vacuum dessicator for 2 days to provide 46.0 g of 6-benzyloxy-3-nitroquinolin-4-ol as a tan powder.

Workup

  1. temperaturewhile maintaining the reaction temperature below 120° C
  2. additionAfter the addition
  3. temperatureto cool to ambient temperature
  4. customThe resulting solid was isolated by filtration
  5. washwashed sequentially with propionic acid, isopropanol, and diethyl ether
  6. customThe material was dried in a vacuum dessicator for 2 days

Sources & evidence

ORD record
ord-aad4b494b67c4ed1ac25a46bf5d17961
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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