Nitric Acid → HCID 18519618, compound

HRID 277412Notes

Reaction equation

HRID 277412 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])=[CH:4][C:3]=1[OH:20].[N+:21]([O-])([OH:23])=[O:22]>>[Cl:1][C:2]1[C:3]([OH:20])=[C:4]([N+:21]([O-:23])=[O:22])[C:5]([N:9]2[C:10](=[O:19])[C:11]3=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]3[C:13]2=[O:14])=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 18519624HCID 18519624, compound

Product 1

HCID 18519618HCID 18519618, compound

Procedure

2-Chloro-4-fluoro-5-(phthalimido)phenol (5.0 g, 17.1 mmol) was slowly added with stirring to con. nitric acid (50 ml) at −10° C. Solution was then warned to ambient temperature. and allowed to stir for 0.5 hr. Addition to ice-water resulted in a light yellow precipitate which was separated by filtration to afford the title compound (5.5 g); 1H NMR (CDCl3+CD3OD, 300 MHz) 4.36 (H, br s), 7.61 (1H, d, J=8.6 Hz), 7.88 (2H, dd, J=3.0, 5.5 Hz), 7.99 (2H, dd, J=3.0, 5.5 Hz) ppm.

Workup

  1. customat −10° C
  2. customwas then warned to ambient temperature
  3. stirringto stir for 0.5 hr
  4. customresulted in a light yellow precipitate which
  5. customwas separated by filtration

Sources & evidence

ORD record
ord-9a943c436c7e42c3bce78f0ea844bbc3
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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