2-Phenoxyethanamine → 5-{[6-(Benzyloxy)-3-nitroquinolin-4-yl]amino}pentan-1-ol

HRID 2383142Notes

Reaction equation

HRID 2383142 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[C:12]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:30][C:31]1C=[C:39]2[C:34](C(Cl)=C([N+]([O-])=O)C=[N:38]2)=[CH:33][CH:32]=1)C1C=CC=CC=1.NCCCCCO.O(CCN)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[C:12]2[NH:38][CH2:39][CH2:34][CH2:33][CH2:32][CH2:31][OH:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 156512-PhenoxyethanamineHCID 756345-Aminopentan-1-ol2×HCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinolineHCID 670509926-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 670509595-{[6-(Benzyloxy)-3-nitroquinolin-4-yl]amino}pentan-1-ol

Procedure

A modification of the general method described in Part A of Example 46 was followed using 6-benzyloxy-4-chloro-3-nitroquinoline (10.5 g, 34 mmol), prepared as described in Parts A-D of Example 57, in lieu of 7-benzyloxy-4-chloro-3-nitroquinoline and 5-amino-1-pentanol (3.5 g, 34 mmol) in lieu of 2-phenoxyethylamine. The reaction was heated at reflux for two hours and then allowed to cool to ambient temperature slowly and stirred overnight. An analysis by TLC indicated the presence of starting material, and additional 5-amino-1-pentanol (0.2 equivalent) was added. The reaction was heated at reflux until the reaction was complete as indicated by TLC. Following the work-up, the crude product was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol) to provide 5.95 g of 5-{[6-(benzyloxy)-3-nitroquinolin-4-yl]amino}pentan-1-ol as a yellow solid.

Workup

  1. customprepared
  2. temperatureThe reaction was heated
  3. temperatureat reflux for two hours
  4. additionwas added
  5. temperatureThe reaction was heated
  6. temperatureat reflux until the reaction
  7. customthe crude product was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-f4fc54ad95474aef955a97f790926736
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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