Dimethyl 4-hydroxy-3-nitrophthalate → Dimethyl 3-amino-4-hydroxyphthalate

HRID 2277125Notes

Reaction equation

HRID 2277125 reaction equation
[OH:1][C:2]1[C:3]([N+:16]([O-])=O)=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]>CO.[Pd]>[NH2:16][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 1

HCID 19800652Dimethyl 4-hydroxy-3-nitrophthalate

Product 1

HCID 19800642Dimethyl 3-amino-4-hydroxyphthalateYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the crude dimethyl 4-hydroxy-3-nitrophthalate C1-3 (25 g, 98 mmol) and Pd/C (1.0 g) in CH3OH (400 mL) was stirred at room temperature overnight under H2 atmosphere. LCMS showed that the reaction was complete. The reaction mixture was filtered through a celite pad and the filtrate was evaporated in vacuo. The residue was purified by chromatography (silica gel, PE:EA (1:1, v:v)) to yield compound C1-4 as a yellow solid (11.5 g, yield: 52%). 1H NMR (DMSO-d6, 400 MHz) δ: 10.45 (s, 1H), 6.89 (d, J=8 Hz, 1H), 6.37 (d, J=8 Hz, 1H), 5.19 (s, 2H), 3.75 (s, 3H), 3.72 (s, 3H); MS (ESI+): m/z 226 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by chromatography (silica gel, PE:EA (1:1, v:v))

Sources & evidence

ORD record
ord-355dcfa92a4a4e859acf8ab4d0c2cee5
Source dataset
uspto-grants-2015_09
Patent number
US09133161B2

Reaction notes

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