HCID 57742139, compound → HCID 12370790, compound

HRID 1626846Notes

Reaction equation

HRID 1626846 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>[C].[Pd].C1COCC1.CCO>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 1

HCID 57742139HCID 57742139, compound

Product 1

HCID 12370790HCID 12370790, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To the flask was added THF/EtOH (1:1, 30 mL) followed by Ethyl 2-(3-hydroxy-4-nitrophenyl)propanoate (900 mg, 3.76 mmol) and 10% palladium carbon (93 mg) at room temperature. The reaction mixture was hydrogenated and stirred for 1 hrs at 46 psi then filtered through celite bed, and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:2) as eluant.

Workup

  1. filtrationthen filtered through celite bed
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-6ae3daa5c00d4f6e80589f1959307566
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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