Aniline → HCID 178468312, compound

HRID 1805426Notes

Reaction equation

HRID 1805426 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[C:17]([CH2:20][C:21](=[O:23])[CH3:22])(=[O:19])[CH3:18]>C(O)(=O)C.Cl.O.C(O)C>[C:2]1([NH:1][N:8]=[C:20]([C:21](=[O:23])[CH3:22])[C:17](=[O:19])[CH3:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 6115AnilineHCID 31261AcetylacetoneHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468312HCID 178468312, compoundYield 67.3%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of aniline (2000 mg, 21.50 mmol) in 30 mL of acetic acid and 5 mL of concentrated hydrochloride solution, sodium nitrite (1780 mg, 25.80 mmol) in 8 mL of water was added dropwise at 0° C., and the mixture was stirred at 0° C. for 1 h. Then to the reaction mixture was added dropwise a solution of sodium acetate (5290 mg, 64.50 mmol) and acetylacetone (2795 mg, 27.95 mmol) in 20 mL of ethanol and 12 mL of water. The mixture was stirred at room temperature overnight, filtered, washed with water, EtOH/H2O (1:1) and hexane, and dried to give 3-(phenylhydrazono)pentane-2,4-dione (2955 mg, 67%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationfiltered
  3. washwashed with water, EtOH/H2O (1:1) and hexane
  4. customdried

Sources & evidence

ORD record
ord-f2875beca24d4d2ba6ab7b69c96aa326
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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