4-Aminobenzoic Acid → HCID 178472850, compound

HRID 564747Notes

Reaction equation

HRID 564747 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[N:11]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21][C:22]([CH3:24])=[O:23]>Cl.O.C(O)C>[CH2:27]([O:26][C:20]([C:21](=[N:11][NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[C:22](=[O:23])[CH3:24])=[O:25])[CH3:28]

Participants

8

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 8868Ethyl AcetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178472850HCID 178472850, compoundYield 98.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

4-Amino-benzoic acid (40 g, 0.28 mol) was dissolved in a mixture of concentrated hydrochloric acid (84 ml) and water (84 ml). To the resulting mixture was added dropwise at 5° C. a solution of sodium nitrite (21.5 g, 0.31 mol) in water (100 ml). The resulting diazonium salt was added to a mixture of sodium acetate (116 g, 0.85 mol), ethanol (300 ml) and ethyl acetoacetate (36.5 ml, 0.28 mol) at room temperature. The resulting mixture was diluted with a 50% aqueous ethanol (1 l) and stirred for 1 h at room temperature. The precipitate was filtered off and washed with water (1 l), 50% aqueous ethanol (1 l) and heptane (2×300 ml) and dried in vacuo at 50 ° C. for 48 h affording 77 g (98%) of 4-[N′-(1-ethoxycarbonyl-2-oxo-propylidene)-hydrazino]-benzoic acid as a solid.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water (1 l), 50% aqueous ethanol (1 l) and heptane (2×300 ml)
  3. customdried in vacuo at 50 ° C. for 48 h

Sources & evidence

ORD record
ord-c35f79f4523549cd97f6a30070f9e7cf
Source dataset
uspto-grants-2001_01
Patent number
US06169087A

Reaction notes

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