HCID 10547737, compound → HCID 10521771, compound

HRID 610623Notes

Reaction equation

HRID 610623 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([N+:24]([O-])=O)[CH:20]=4)[CH2:15]3)=[N:11][CH:10]=[N:9]2)=[CH:5][CH:4]=1>CO.[Pd]>[NH2:24][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([CH2:13][C:12]1[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=3)[N:9]=[CH:10][N:11]=1)[CH2:23][CH2:22]2

Participants

4

Reactant 1

HCID 10547737HCID 10547737, compound

Product 1

HCID 10521771HCID 10521771, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[2-(4-Methoxybenzyl)-2H-[1,2,4]triazol-3-ylmethyl]-6-nitro-1,2,3,4-tetrahydro-isoquinoline (0.5 g, 1.3 mmol) was hydrogenated in methanol (25 mL) over 10% Pd/C (0.25 g) at 50 psi (about 345 kPa) for three hours. The reaction mixture was filtered and the solvent was evaporated in vacuo. Ethyl acetate and water were added and the pH was adjusted to 10 with solid sodium carbonate. The layers were separated and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo to an oil; 0.4 g, 87% yield. 1H NMR (CDCl3) δ 7.86 (s, 1), 7.18 (d, 2), 6.79 (m, 3), 6.48 (m, 2), 5.42 (s, 2), 3.76 (s, 3), 3.73 (s, 2), 3.50 (s, 2), 2.80 (m, 2), 2.69 (m, 2). IR (KBr) 1613, 1587, 1513 cm-1. Mass spectrum: m/z: 348 (M+ -1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated in vacuo
  3. additionEthyl acetate and water were added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with additional ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo to an oil

Sources & evidence

ORD record
ord-dd003dd1fd9f4c39a630aa46fda33ca5
Source dataset
uspto-grants-1999_12
Patent number
US05998623

Reaction notes

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