HCID 20309579, compound → HCID 20309512, compound

HRID 1763317Notes

Reaction equation

HRID 1763317 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 further 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°). (Found: M+, 209. C10H11NO4 requires: M, 209).

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-1e9ca27838c0428cab5c4dcb821d6560
Source dataset
uspto-grants-1978_09
Patent number
US04111936

Reaction notes

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