Ethanol → HCID 67264095, compound

HRID 1041067Notes

Reaction equation

HRID 1041067 reaction equation
[CH2:1]([NH:3][C:4](=[O:21])[N:5]([CH2:18][CH2:19][OH:20])[CH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=1[O:16][CH3:17])[CH3:2].C(O)C>[Pd]>[NH2:13][C:11]1[CH:10]=[CH:9][C:8]([O:16][CH3:17])=[C:7]([CH:12]=1)[CH2:6][N:5]([CH2:18][CH2:19][OH:20])[C:4]([NH:3][CH2:1][CH3:2])=[O:21]

Participants

4

Reactant 2

HCID 702EthanolHCID 67264053HCID 67264053, compound

Product 1

HCID 67264095HCID 67264095, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-Ethyl-1-(2-hydroxy-ethyl)-1-(2-methoxy-5-nitro-benzyl)-urea (0.43 g, 0.0014 mol) in Ethanol (50 mL, 0.8 mol) was hydrogenated with 10% Pd/C (10:90, Palladium:carbon black, 0.027 g) catalyst overnight. The reaction was filtered and the filtrate evaporated to give 1-(5-Amino-2-methoxy-benzyl)-3-ethyl-1-(2-hydroxy-ethyl)-urea as a yellow oil (0.40 g, 75%). 0.020 g was chromatographed on Alumina with DCM/IPA (20-1) giving 1-(5-Amino-2-methoxy-benzyl)-3-ethyl-1-(2-hydroxy-ethyl)-urea as an oil (0.010 g). LCMS (m/e) 268 (M+1); 1H-NMR (DMSO, 400 MHz) δ 6.68 (d, 1H, J=8.59 Hz),6.44-6.39 (d, 1H, J=9.6 Hz), 6.32 (s, 1H), 6.26-6.23 (t, 1H, J=5.30 Hz), 4.79-4.76 (t, 1H, J=5.06 Hz), 4.59 (s, 2H), 4.15 (s, 2H), 3.65 (s, 3H), 3.47-3.43 (q, 2H, J=5.30 Hz), 3.20-3.17 (t, 2H, J=6.06 Hz), 3.08-3.00 (q, 2H, J=5.81 Hz), 1.07-0.98 (t, 3H, J=7.07 Hz).

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-be8133fce2f1447abbc78419f83126fc
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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