(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amine → 7-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine

HRID 2383101Notes

Reaction equation

HRID 2383101 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][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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>C1(C)C=CC=CC=1.[Pt]>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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

4

Reactant 1

HCID 67050949(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amine

Product 1

HCID 670509287-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamineYield 104.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent2×

Procedure

(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amine (14.24 g, 34.28 mmol) was dissolved in toluene (900 mL) with heating and added to a Parr vessel charged with 5% platinum on carbon (6.7 g, 34.28 mmol) and toluene (100 mL). The vessel was placed under hydrogen pressure (35 psi, 2.4×105 Pa) and shaken for two hours. The catalyst was removed by filtration and washed with hexanes and dichloromethane. The filtrate was concentrated under reduced pressure, and the residue was recrystallized from methanol, isolated by filtration, washed with hexanes, and dried under high vacuum to provide 13.82 g of 7-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine as a solid.

Workup

  1. temperaturewith heating
  2. additionadded to a Parr vessel
  3. customThe catalyst was removed by filtration
  4. washwashed with hexanes and dichloromethane
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was recrystallized from methanol
  7. customisolated by filtration
  8. washwashed with hexanes
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-2269ec158a294aecad816e12ee8da957
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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