Water → 8-Amino-6-methoxy-4-methyl-5-[7-phenylheptoxy]quinoline

HRID 1111384Notes

Reaction equation

HRID 1111384 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:5]2[C:10](=[C:11]([N+:13]([O-])=O)[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH3:16].O.O(CCCC)CCCC>[Fe].CC(O)=O>[NH2:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[C:4]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[C:6]2[CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 8909Butyl etherHCID 6163856-Methoxy-4-methyl-8-nitro-5-(7-phenylheptoxy)quinoline

Product 1

HCID 6091518-Amino-6-methoxy-4-methyl-5-[7-phenylheptoxy]quinolineYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 6-methoxy-4methyl-8-nitro-5-(7-phenylheptoxy) quinoline [Example 1b](2.0 g, 0.005 mol) de-greased 40 mesh Fe filings (5 g) H2O (20 ml), HOAc (4 ml) and n-Bu2O was heated at 80°-85° C. for 1 h, cooled and filtered. The solid was thoroughly extracted with Et2O (500 ml) and the extract was dried (Na2SO4) treated with charcoal and concentrated to an oil. Crystallization from pet ether gave 1.6 g (85%) of 8-amino-6-methoxy-4-methyl-5-(7-phenylheptoxy) quinoline as yellow green crystals, mp 61°-63° C. A second crystallization from pet ether (Darco) provided the analytical sample as glistening yellow crystals, mp 64°-65° C.

Workup

  1. temperaturewas heated at 80°-85° C. for 1 h
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionThe solid was thoroughly extracted with Et2O (500 ml)
  5. dry with materialthe extract was dried (Na2SO4)
  6. additiontreated with charcoal
  7. concentrationconcentrated to an oil
  8. customCrystallization from pet ether

Sources & evidence

ORD record
ord-1b31cd39b3164bfe8e3144cadc94f3bc
Source dataset
uspto-grants-1990_12
Patent number
US04980360

Reaction notes

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