N-(3-(tert-Butyldimethylsilyloxy)propyl)-3-nitroquinolin-4-amine → N4-(3-(tert-Butyldimethylsilyloxy)propyl)quinoline-3,4-diamine

HRID 2090252Notes

Reaction equation

HRID 2090252 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[N+:23]([O-])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)(=O)C.CO.[Fe]>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[NH2:23])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 68429388N-(3-(tert-Butyldimethylsilyloxy)propyl)-3-nitroquinolin-4-amine

Product 1

HCID 86647172N4-(3-(tert-Butyldimethylsilyloxy)propyl)quinoline-3,4-diamine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Iron powder (10 g) was added to a solution of the product from step (ii) (20 g) in acetic acid (200 mL) and MeOH (100 mL). The mixture was stirred at rt for 30 min then evaporated under reduced pressure. The residue was partitioned between DCM and water, the organics separated, washed with aq NaHCO3 solution, water, dried, and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 3-5% MeOH in DCM to give a brown oil, 10.1 g.

Workup

  1. customthen evaporated under reduced pressure
  2. customThe residue was partitioned between DCM and water
  3. washthe organics separated, washed with aq NaHCO3 solution, water
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography on silica eluting with 3-5% MeOH in DCM
  7. customto give a brown oil, 10.1 g

Sources & evidence

ORD record
ord-558b321140e8473e8094100b0b1a0815
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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