5-Chloro-2-nitroaniline → HCID 21834282, compound

HRID 1740884Notes

Reaction equation

HRID 1740884 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[N+:14]([C:17]1[CH:23]=[CH:22][C:21](Cl)=[CH:20][C:18]=1[NH2:19])([O-:16])=[O:15]>CN(C)C=O>[NH2:19][C:18]1[CH:20]=[C:21]([O:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[CH:22]=[CH:23][C:17]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 742185-Chloro-2-nitroanilineHCID 23665647Potassium tert-butoxideHCID 178418642HCID 178418642, compound

Product 1

HCID 21834282HCID 21834282, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
17.5 °C

Procedure

A 2-liter round-bottomed flask is charged with 35.2 g (0.369 mol) of 4-hydroxypyridine and 250 ml of anhydrous dimethylformamide (DMF). Under nitrogen, 42 g (0.369 mol) of potassium tert-butylate are added portionwise while the temperature is maintained at 15-20° C. with a water/ice bath. After the addition, the mixture is stirred for 2 hours and a pale yellow solution is obtained. 60 g (0.358 mol) of 2-nitro-5-chloroaniline are then added and an intense red coloration is obtained. The mixture is brought to 100° C. for 6 hours and then allowed to cool overnight. The DMF is evaporated off and water is then added; a precipitate is obtained, which is filtered off and washed with isopropanol in the heated state and then dried.

Workup

  1. additionAfter the addition
  2. customa pale yellow solution is obtained
  3. customan intense red coloration is obtained
  4. waitThe mixture is brought to 100° C. for 6 hours
  5. temperatureto cool overnight
  6. customThe DMF is evaporated off
  7. additionwater is then added
  8. customa precipitate is obtained
  9. filtrationwhich is filtered off
  10. washwashed with isopropanol in the heated state
  11. customdried

Sources & evidence

ORD record
ord-4fbe12e40aaa44d48d934f699e4585e0
Source dataset
uspto-grants-1999_10
Patent number
US05972968

Reaction notes

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