Nitric Acid → HCID 178418967, compound

HRID 9361

Reaction equation

HRID 9361 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:17])=[CH:12][CH:13]=[N:14]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:18]([O-])([OH:20])=[O:19]>C(O)(=O)CC>[N+:18]([C:12]1[CH:13]=[N:14][C:15]2[C:10]([C:11]=1[OH:17])=[CH:9][CH:8]=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH:16]=2)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178418977HCID 178418977, compound

Product 1

HCID 178418967HCID 178418967, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
129 °C

Procedure

A stirred suspension of 7-phenylquinolin-4-ol (84.9 g, 384 mmol) in propionic acid (850 mL) was heated to 129° C. Nitric acid (70%, 45.0 g) was added dropwise over 25 min, during which the temperature dropped to 124° C. The reaction was stirred an additional 3 h at that temperature and then cooled to 5° C. on an ice bath. The resulting solid was collected by filtration, washed with ice cold ethanol (until washings were nearly colorless) and dried at 70° C. in a vacuum oven overnight to obtain 83.2 g of 3-nitro-7-phenylquinolin-4-ol as a beige powder.

Workup

  1. additiondropped to 124° C
  2. temperaturecooled to 5° C. on an ice bath
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with ice cold ethanol (until washings
  5. customdried at 70° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-e52aec0cac81483fa1aff8a997e54a25
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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