t-Butyl (6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinyl)carbamate → t-Butyl (8-amino-1,2,3,4-tetrahydro-3-quinolyl)carbamate

HRID 327456Notes

Reaction equation

HRID 327456 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[NH:8][CH2:7][CH:6]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:5]2.[H][H]>[Pd].C(O)C>[NH2:12][C:10]1[CH:11]=[CH:2][CH:3]=[C:4]2[C:9]=1[NH:8][CH2:7][CH:6]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:5]2

Participants

5

Reactant 2

HCID 15937762t-Butyl (6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 19108500t-Butyl (8-amino-1,2,3,4-tetrahydro-3-quinolyl)carbamateYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of t-butyl (6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinyl)-carbamate (3.72 g, 0.01 mol), absolute ethanol (150 mL) and 10% palladium on carbon (0.60 g) was hydrogenated (50 lb hydrogen pressure) for 18 hours. The mixture was filtered through celite and the solvent removed. The residual foam was partitioned between ethyl acetate and 1 N sodium hydroxide, and the ethyl acetate phase was evaporated under reduced pressure to give 2.72 g of t-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolyl)carbamate (compound XXXII) as an oil.

Workup

  1. customfor 18 hours
  2. filtrationThe mixture was filtered through celite
  3. customthe solvent removed
  4. customThe residual foam was partitioned between ethyl acetate and 1 N sodium hydroxide
  5. customthe ethyl acetate phase was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f35d940636a9437195fb14e38227a8a0
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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