tert-Butyl 7-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate → tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1021418Notes

Reaction equation

HRID 1021418 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 6420695tert-Butyl 7-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 22061016tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylateYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl 7-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate (9.4 g, 34 mmol) in ethanol (150 mL) was treated with 10% palladium on carbon (0.5 g), and the resulting mixture was hydrogenated on a Parr shaker at an initial pressure of 40 psi for 30 minutes. The catalyst was removed by filtration through a glass microfibre filter, and the filtrate was concentrated. The residue was purified by chromatography on silica gel, eluting with 75/25 to 70/30 hexanes/ethyl acetate, to afford tert-butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate as a yellow oil (6.6 g, 79% yield).

Workup

  1. customfor 30 minutes
  2. customThe catalyst was removed by filtration through a glass microfibre
  3. filtrationfilter
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography on silica gel
  6. washeluting with 75/25 to 70/30 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-52555f7966484f649dea980b1e7a57f1
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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