Ethanol → Dimethyl 3-amino-4-hydroxyphthalate

HRID 1646451Notes

Reaction equation

HRID 1646451 reaction equation
[N+:1]([C:4]1[C:13]([OH:14])=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[C:15]([O:17][CH3:18])=[O:16])([O-])=O.C(O)C.C(OCC)(=O)C>[Pt].C(Cl)Cl>[NH2:1][C:4]1[C:13]([OH:14])=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 19800652Dimethyl 4-hydroxy-3-nitrophthalate

Product 1

HCID 19800642Dimethyl 3-amino-4-hydroxyphthalate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of dimethyl 3-nitro-4-hydroxyphthalate (28.9 g, 0.113 mol), ethanol and 5% platinum on carbon (2.80 g, 50% aqueous) is shaken on a Parr hydrogenator under hydrogen for 1.75 hours at room temperature. The reaction mixture is filtered through diatomaceous earth and the filtrate is concentrated in vacuo to give a pale green solid residue. Chromatography (silica gel, ethyl acetate:methylene chloride eluent) affords the title product as a pale yellow solid, 3.69 g, mp 112°-113° C., identified by NMR and IR spectral analyses.

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. concentrationthe filtrate is concentrated in vacuo
  3. customto give a pale green solid residue

Sources & evidence

ORD record
ord-5b5dc28bd8314f7ab9dea2f662cb3f4d
Source dataset
uspto-grants-1993_01
Patent number
US05180419

Reaction notes

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