HCID 21919924, compound → HCID 21919996, compound

HRID 1438102Notes

Reaction equation

HRID 1438102 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([N:14]([C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])=[N:9][CH:8]=[CH:7]2)([O-])=O.[H][H]>CO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([N:14]([C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[C:15]([C:17]([CH3:19])([CH3:20])[CH3:18])=[O:16])=[N:9][CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 21919924HCID 21919924, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21919996HCID 21919996, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

6-Nitro-1-bis(tert-butyl carbonyl)aminoisoquinoline (75.00 g, 0.193 mol) in methanol/THF (500 ml/500 ml) was hydrogenated with a hydrogen balloon in the presence of Pd/C (5%, 5 g) for 2.0 h. Filtration of the Pd/C and concentration gave a solid, which was recrystallized from methanol to give 65.72 g (94.97%) of 1B as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.33 (m, 18H) 4.18 (s, 2H) 6.89 (d, J=2.20 Hz, 1H) 6.99 (dd, J=9.01, 2.42 Hz, 1H) 7.35 (d, J=6.59 Hz, 1H) 7.75 (d, J=8.79 Hz, 1H) 8.22 (d, J=5.71 Hz, 1H). LC-MS: 741 (2M+Na)+.

Workup

  1. filtrationFiltration of the Pd/C and concentration
  2. customgave a solid, which
  3. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-dfb4c38b03134561808190b7fa0dbfae
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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