Ethanol → HCID 59199444, compound

HRID 2089534Notes

Reaction equation

HRID 2089534 reaction equation
[CH:1]([O:4][C:5]([C:7]1[N:8]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-])=O)[CH:20]=3)[CH2:15][CH2:14][CH2:13]2)[CH:9]=[N:10][CH:11]=1)=[O:6])([CH3:3])[CH3:2].[CH2:25]([OH:27])[CH3:26]>[Pd]>[CH:1]([O:4][C:5]([C:7]1[N:8]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:22][C:25](=[O:27])[CH3:26])[CH:20]=3)[CH2:15][CH2:14][CH2:13]2)[CH:9]=[N:10][CH:11]=1)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 59199321HCID 59199321, compound

Product 1

HCID 59199444HCID 59199444, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 3-(7-nitro-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester, which can be prepared as described in Example 5, (3.24 g, 9.84 mmol) in ethanol (125 mL) is added palladium on carbon (10% wt., 0.65 g, 0.61 mmol). The flask is flushed with hydrogen and stirred under balloon pressure at room temperature overnight. The catalyst is then filtered through Celite®. The Celite® cake is washed with methanol and the combined filtrate is concentrated to afford 3-(7-acetylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (d, J=6.3 Hz, 3 H), 1.38 (d, J=6.3 Hz, 3 H), 1.62-1.83 (m, 2 H), 2.01-2.08 (m, 1 H), 2.13-2.21 (m, 1 H), 2.67-2.84 (m, 2 H), 5.22 (sept, J=6.3 Hz, 1 H), 6.17 (t, J=5.1 Hz, 1 H), 6.31 (d, J=2.5 Hz, 1 H), 6.62 (dd, J=8.2, 2.5 Hz, 1 H), 6.98 (d, J=8.2 Hz, 1 H), 7.21 (s, 1 H), 7.77 (s, 1 H).

Workup

  1. customThe flask is flushed with hydrogen
  2. filtrationThe catalyst is then filtered through Celite®
  3. washThe Celite® cake is washed with methanol
  4. concentrationthe combined filtrate is concentrated

Sources & evidence

ORD record
ord-abbcadc82503445cb178f8dd88f0c705
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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