Hexane → Methyl 4-amino-3-(2-hydroxyethoxy)benzoate

HRID 1451081Notes

Reaction equation

HRID 1451081 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)[C:8]([O:10][CH3:11])=[O:9].CCCCCC.C(OCC)(=O)C>C(O)C.[Pt]=O>[NH2:15][C:14]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:4][CH2:3][CH2:2][OH:1]

Participants

6

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 10514237Methyl 3-(2-hydroxyethoxy)-4-nitrobenzoate

Product 1

HCID 10560441Methyl 4-amino-3-(2-hydroxyethoxy)benzoateYield 101%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a sample of methyl 3-(2-hydroxyethoxy)-4-nitrobenzoate (3.28 g, 0.0136 mol) dissolved in ethanol was added platinum oxide (50 mg). The mixture was hydrogenated for 40 min at 35 psi. Thin-layer chromatographic analysis (SiO2, 3:2 hexane:ethyl acetate) showed disappearance of starting material along with the formation of a new, lower-running spot (Rf =01) indicating the reaction was complete. The mixture was then filtered through a pad of Celite and the pad washed with fresh ethanol. The filtrate was concentrated and dried in vacuo to give 2.9 g (100%) of methyl 4-amino-3-(2-hydroxyethoxy)benzoate as an off-white solid.

Workup

  1. filtrationThe mixture was then filtered through a pad of Celite
  2. washthe pad washed with fresh ethanol
  3. concentrationThe filtrate was concentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e9dfe333a1214566937b74bc96ce31c8
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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