HCID 20309579, compound → HCID 20309512, compound

HRID 972792Notes

Reaction equation

HRID 972792 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5]>[OH-].[NH4+].O>[NH2:15][C:12]1[CH:13]=[CH:14][C:2]([OH:1])=[C:3]([CH:11]=1)[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5]

Participants

4

Reactant 1

HCID 20309579HCID 20309579, compound

Product 1

HCID 20309512HCID 20309512, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent2×

Procedure

A solution of 3-(2-hydroxy-5-nitrobenzoyl)propionic acid (5.5 g, 0.023 mole) in ammonium hydroxide solution (5N; 100 ml) was added to a stirred, boiling solution of ferrous sulphate heptahydrate (45 g, 0.161 mole) in water (200 ml). Stirring under reflux was continued for a futher 1 hour, ammonium hydroxide solution was added to pH 9, the mixture was filtered through Kieselguhr and evaporated to dryness. The solid residue was crystallised from ethanol to give pale yellow needles of 3-(5-amino-2-hydroxybenzoyl)propionic acid (2.2 g, 46%, m.p. 158°-160°).

Workup

  1. temperatureunder reflux
  2. filtrationthe mixture was filtered through Kieselguhr
  3. customevaporated to dryness
  4. customThe solid residue was crystallised from ethanol

Sources & evidence

ORD record
ord-358db7c46aa84c74a5d230a4bc8885c7
Source dataset
uspto-grants-1977_10
Patent number
US04053601

Reaction notes

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