Toluene → N1-[5-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]benzamide

HRID 746504Notes

Reaction equation

HRID 746504 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[CH2:29](C(CC)(CC)C([O-])([O-])[O-])[CH3:30].C1(C)C=CC=CC=1>[Pt].C(O)(C)C>[CH3:29][C:30]1[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:1]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 21875354TriethylorthoaceateHCID 23512735N-{5-[(3-nitroquinolin-4-yl)amino]pentyl}benzamide

Product 1

HCID 23512678N1-[5-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]benzamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

A catalytic amount of platinum on carbon was added to a suspension of N1-{5-[(3-nitroquinolin-4-yl)amino]pentyl}benzamide (3.4 g, 9 mmol) in isopropyl alcohol (250 mL). The reaction mixture was placed under a hydrogen atmosphere at 50 psi (3.4×104 pascals) on a Parr apparatus. After 2 hours the reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under vacuum to provide crude N1-{5-[(3-aminoquinolin-4-yl)amino]pentyl}benzamide. This material was combined with triethylorthoacetate (1.4 g, 9 mmol) and toluene (200 mL). The reaction mixture was heated overnight on a steam bath with a Vigreux column. The toluene was decanted from the reaction mixture and concentrated under vacuum to provide N1-[5-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]benzamide as an oil.

Workup

  1. filtrationAfter 2 hours the reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under vacuum
  4. customto provide crude N1-{5-[(3-aminoquinolin-4-yl)amino]pentyl}benzamide
  5. temperatureThe reaction mixture was heated overnight on a steam bath with a Vigreux column
  6. customThe toluene was decanted from the reaction mixture
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1677026e3234415caf7b4be9627abfa2
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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