(7-benzyloxy-3-nitroquinolin-4-yl)(tetrahydro-2H-pyran-4-ylmethyl)amine → 7-benzyloxy-N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine

HRID 2426359Notes

Reaction equation

HRID 2426359 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[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.[H][H]>[Pt].C(#N)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[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

5

Reactant 2

HCID 67051153(7-benzyloxy-3-nitroquinolin-4-yl)(tetrahydro-2H-pyran-4-ylmethyl)amineHCID 178418361HCID 178418361, compound

Product 1

HCID 670510957-benzyloxy-N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A 2 L glass parr vessel was charged with of 7-(benzyloxy)-3-nitro-N-(tetrahydro-2H-pyran-4-ylmethyl)quinolin-4-amine (59.34 g, 0.151 mol), platinum on carbon (5%, 6.6 g) and acetonitrile (600 mL) to provide a black mixture. The vessel was placed on a shaker and pressurized with hydrogen gas (−50 psi, 3.4×105 Pa). After shaking for 18 hours at ambient temperature, the mixture was filtered through CELITE filter agent, and the filter cake washed with acetonitrile. The filtrate was concentrated under reduced pressure to provide 7-(benzyloxy)-N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine

Workup

  1. customto provide a black mixture
  2. filtrationthe mixture was filtered through CELITE
  3. filtrationfilter agent
  4. washthe filter cake washed with acetonitrile
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8696966b165049019b2b9523a2d4f34c
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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