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

HRID 2090237Notes

Reaction equation

HRID 2090237 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.[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

4

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 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of the product from step (i) (8.5 g), iron powder (14 g) in acetic acid was stirred at rt for 3 h the partitioned between EtOAc/water. The organics were separated, washed with saturated NaHCO3 solution, brine, dried and evaporated under reduced pressure, yield 4.85 g.

Workup

  1. custompartitioned between EtOAc/water
  2. customThe organics were separated
  3. washwashed with saturated NaHCO3 solution, brine
  4. customdried
  5. customevaporated under reduced pressure, yield 4.85 g

Sources & evidence

ORD record
ord-9a096c20ce294a618e85dd00054c12c5
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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