Ethyl Acetate → HCID 10197784, compound

HRID 1251295Notes

Reaction equation

HRID 1251295 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[CH:11]([OH:13])[CH3:12].[H][H].C(OCC)(=O)C>CO.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH:11]([OH:13])[CH3:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11148092Benzeneethanol,2-amino-5-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 10197784HCID 10197784, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Catalytic hydrogenation of 6 (27.0 g, 150 mmole) under 60 psi hydrogen pressure with 10% Pd/C (2.7 g) in anhydrous MeOH (150 mL)/ethyl acetate (150 mL) was completed in 2.5 h. The catalyst was removed by filtration over Celite. The filtrate was evaporated under vacuum to afford 1-(2,5-diamino-phenyl)-ethanol 1 (22.83 g, 100 % yield). Mp 124° C.; 1HNMR (400 MHz, DMSO-d6) δ1.26 (d, 3H, J=6.4 Hz), 4.15 (d, 4H, J=10.7 Hz), 4.61-4.65 (m, 1H), 4.94 (d, 1H, J=3.6 Hz), 6.24 (dd, 1H, J=2.5, 8.2 Hz), 6.36 (d, 1H, J=8.2 Hz), 6.45 (d, 1H, J=2.5 Hz); MS m/z 152 (M+); Anal. Calcd. for C8H12N2O: C, 63.13. H, 7.95. N, 18.41.O, 10.51. Found: C, 62.83. H, 7.90. N, 18.46. O, 10.17.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-1dd5526dec3c4c79946e87923c6c075b
Source dataset
uspto-grants-2002_01
Patent number
US06342079B1

Reaction notes

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