Hydrochloric Acid → HCID 54732146, compound

HRID 904295Notes

Reaction equation

HRID 904295 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.C([O-])(=O)C.[Na+].[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[Cl:26])N.Cl.N([O-])=O.[Na+]>O.CC(C)=O>[Cl:18][C:19]1[CH:20]=[C:21]([C:3]2[C:4](=[O:12])[O:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:23]=[CH:24][C:25]=1[Cl:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 72573,4-Dichloroaniline2×HCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 546829304-Hydroxycoumarin

Product 1

HCID 54732146HCID 54732146, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

33.8 g. (0.21 mol) of 4-hydroxy-coumarin, 140 ml. of acetone, 40 g. of sodium acetate and 6.6 g. of cuprous chloride are placed in a one-liter reactor. The mixture is brought to a temperature lower than 5° C. There are then added dropwise a solution of the diazonium chloride of 3,4-dichloro-aniline, prepared from 32.4 g. (0.2 mol) of 3,4-dichloro-aniline, 80 ml. of concentrated hydrochloric acid, 120 ml. of water and 20 g. (0.33 mol) of sodium nitrite. A slight liberation of nitrogen is found. The substance is left for one hour between -8° C. and -5° C. and it is then brought for one hour to 50° C. The acetone is then evaporated under vacuum. A pH value of 1 is adjusted. The chestnut-coloured precipitate is taken up under heat in 2 liters of a 5% solution of sodium bicarbonate, followed by filtration and then the filtrate is acidified with HCl. The product obtained is recovered, washed with water, dried and recrystallised from a mixture of ethanol and water (70-30). A chestnut-coloured product is obtained. Weight 9.8 g.; yield 16% (theoretical yield 51.4 g.); M.P. 262° C.

Workup

  1. customis brought to a temperature lower than 5° C
  2. customprepared from 32.4 g
  3. customThe acetone is then evaporated under vacuum
  4. temperatureunder heat in 2 liters of a 5% solution of sodium bicarbonate
  5. filtrationfollowed by filtration
  6. customThe product obtained
  7. customis recovered
  8. washwashed with water
  9. customdried
  10. customrecrystallised from a mixture of ethanol and water (70-30)
  11. customA chestnut-coloured product is obtained

Sources & evidence

ORD record
ord-75022df387134bcdb3d516010b3cc11f
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

Loading…