5-Nitrosalicylic acid → HCID 9882573, compound

HRID 2298233Notes

Reaction equation

HRID 2298233 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=O)[C:7]([OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:14][C:15]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:16]=1[NH2:17].P(Cl)(Cl)Cl>ClC1C=CC=CC=1>[F:14][C:15]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:16]=1[NH:17][C:9]([C:8]1[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[OH:13])=[O:11]

Participants

5

Reactant 3

HCID 73185-Nitrosalicylic acidHCID 97092,4-DifluoroanilineHCID 24387Phosphorus trichloride

Product 1

HCID 9882573HCID 9882573, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 5-nitrosalicylic acid (1.4 g, 7.7 mmol) and 2,4-difluoroaniline (0.8 mL, 7.7 mmol) in chlorobenzene (40 mL) was treated with PCl3 (0.338 mL, 3.8 mmol). The solution was heated at reflux under an argon atmosphere. After 2 h. the solution was filtered hot and the filtrate was left standing at RT. After 18 h the solution was filtered and the solid was recrystallized from MeOH to give the title compound (0.733 g, 35% yield): 1H NMR (400 MHz, DMSO-d6) δ 2.5-2.6 (s, 3H), 7.1-8.9 (m, 6H), 10.6-10.7 (s, 1H)

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux under an argon atmosphere
  3. filtrationAfter 2 h. the solution was filtered hot
  4. waitthe filtrate was left
  5. customstanding at RT
  6. filtrationAfter 18 h the solution was filtered
  7. customthe solid was recrystallized from MeOH

Sources & evidence

ORD record
ord-8bed730f5c464ab0a0c89d54deec7e6f
Source dataset
uspto-grants-2002_12
Patent number
US06492425B1

Reaction notes

Loading…