7-(benzyloxy)-N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-nitroquinolin-4-amine → HCID 66649879, compound

HRID 419290Notes

Reaction equation

HRID 419290 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:22][CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[C:14]([N+:19]([O-])=O)[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pt].C(#N)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:22][CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])=[C:14]([NH2:19])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 666500237-(benzyloxy)-N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-nitroquinolin-4-amine

Product 1

HCID 66649879HCID 66649879, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent2×

Procedure

A 3-liter stainless steel Parr vessel was charged sequentially with 5% platinum on carbon catalyst, acetonitrile (250 mL), 7-(benzyloxy)-N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-nitroquinolin-4-amine (102 g, 0.225 mol), and additional acetonitrile (1250 mL). The vessel was evacuated and charged with hydrogen gas (30 psi, 2.1×105 Pa). The vessel was shaken overnight. The reaction mixture was then filtered through a layer of CELITE filter agent. The filter cake was rinsed with additional acetonitrile (2 L), and the combined filtrates were concentrated under reduced pressure to provide 95 g of 7-(benzyloxy)-N4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)quinoline-3,4-diamine as an orange-green solid.

Workup

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen gas (30 psi, 2.1×105 Pa)
  3. filtrationThe reaction mixture was then filtered through a layer of CELITE filter agent
  4. washThe filter cake was rinsed with additional acetonitrile (2 L)
  5. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-90ccdb7fc3e349d28fceb07e2641bdde
Source dataset
uspto-grants-2012_01
Patent number
US08093390B2

Reaction notes

Loading…