Tert-butyl 1-(4-nitrophenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate → Tert-butyl 1-(4-aminophenylsulfonyl)1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 2389557Notes

Reaction equation

HRID 2389557 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:14]2)(=[O:12])=[O:11])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 59400179Tert-butyl 1-(4-nitrophenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 59400239Tert-butyl 1-(4-aminophenylsulfonyl)1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-butyl 1-(4-nitrophenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (4.12 g, 9.50 mmol) and palladium on carbon (10% w/w, 0.41 g) in methanol was stirred in an hydrogen atmosphere at room temperature for 18 hours. After filtering through a Celite (10 g) and evaporating to dryness the residue was dried under vacuum overnight to give tert-butyl 1-(4-aminophenylsulfonyl)1,2,3,4-tetrahydroquinolin-3-ylcarbamate.

Workup

  1. filtrationAfter filtering through a Celite (10 g)
  2. customevaporating to dryness the residue
  3. customwas dried under vacuum overnight

Sources & evidence

ORD record
ord-41c6198eb7c646078c0b871352a42112
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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