HCID 20309579, compound → HCID 20309512, compound

HRID 1579283Notes

Reaction equation

HRID 1579283 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) in ammonium hydroxide solution (5N; 100 ml) was added to a stirred, boiling solution of ferrous sulphate heptahydrate (45 g) in water (200 ml). Stirring under reflux was continued for a further 60 minutes, ammonium hydroxide solution was added until the mixture had pH 9, the reaction mixture filtered through Kieselguhr and the filtrate 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°C; M+, 209, M, 209).

Workup

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

Sources & evidence

ORD record
ord-81bcd18539f2440498a6c781085489df
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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