Nitric Acid → HCID 178526778, compound

HRID 913348Notes

Reaction equation

HRID 913348 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([OH:19])=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[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:18]=[C:17]2[C:12]([C:13]([OH:19])=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178516454HCID 178516454, compound

Product 1

HCID 178526778HCID 178526778, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 7-benzyloxyquinolin-4-ol (71.47 g, 0.2844 mol) and propionic acid (700 mL) was heated to 125° C. with vigorous stirring. Nitric acid (23.11 mL of 16 M) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121° C. and 125° C. After the addition, the reaction was stirred at 125° C. for 1 hour then allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7-benzyloxy-3-nitroquinolin-4-ol as a grayish powder. 1H NMR (300 MHz, DMSO-d6) δ 12.77 (s, 1H), 9.12 (s, 1H), 8.17 (dd, J=3.3, 6.3 Hz, 1H), 7.51-7.33 (m, 5H), 7.21-7.17 (m, 2H), 5.25 (s, 2H).

Workup

  1. temperaturewhile maintaining the reaction temperature between 121° C. and 125° C
  2. additionAfter the addition
  3. temperatureto cool to ambient temperature
  4. customThe resulting solid was isolated by filtration
  5. washwashed with water
  6. customdried in an oven for 1.5 days

Sources & evidence

ORD record
ord-21fe559ca41b4871b25e3b012047556a
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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