Nitric Acid → HCID 178486766, compound

HRID 1042982Notes

Reaction equation

HRID 1042982 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[C:10]([C:11]2[CH:20]=[C:19]3[C:14]([C:15]([OH:21])=[CH:16][CH:17]=[N:18]3)=[CH:13][CH:12]=2)=[C:9]([CH3:22])[O:8][N:7]=1.[C:23](O)(=[O:26])CC>>[CH3:5][C:6]1[C:10]([C:11]2[CH:20]=[C:19]3[C:14]([C:15]([OH:21])=[C:16]([N+:1]([O-:4])=[O:2])[CH:17]=[N:18]3)=[CH:13][C:12]=2[O:26][CH3:23])=[C:9]([CH3:22])[O:8][N:7]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1032Propionic AcidHCID 178434741HCID 178434741, compound2×

Product 1

HCID 178486766HCID 178486766, compoundYield 82%

Conditions

Temperature
100 °C

Procedure

Nitric acid (10 ml) was added slowly to a solution of 7-(3,5-dimethyl-4-isoxazolyl)-4-quinolinol (for a preparation see Intermediate 14 (28 g, 104 mmol) in propanoic acid (450 ml) at room temperature, followed by heating the reaction mixture to 100° C. for 1 h. After cooling with an ice bath, the precipitate was filtered off, washed with pentane to give the title compound as a yellow powder (27 g, 82%). [APCI-MS] m/z: 314 [M−H]−, Rt 2.12 min. 1H NMR (300 MHz, DMSO-d6, ppm) δ: 13.06 (s, 1H), 9.26 (s, 1H), 7.84 (s, 1H), 7.67 (s, 1H), 3.98 (s, 3H), 2.39 (s, 3H), 2.19 (s, 3H).

Workup

  1. customat room temperature
  2. temperatureAfter cooling with an ice bath
  3. filtrationthe precipitate was filtered off
  4. washwashed with pentane

Sources & evidence

ORD record
ord-a1a92247eb6d43df871f2f0762d207ce
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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