Water → 8-Amino-6-methoxy-4-methyl-5-(4-phenylbutoxy)quinoline

HRID 1030187Notes

Reaction equation

HRID 1030187 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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 5635176-Methoxy-4-methyl-8-nitro-5-[4-phenylbutoxy]quinoline

Product 1

HCID 6091458-Amino-6-methoxy-4-methyl-5-(4-phenylbutoxy)quinolineYield 66%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 6-methoxy-4-methyl-8-nitro-5-(4-phenylbutoxy) quinoline (3.7 g, 0.01 mol), degreased 40 mesh Fe filings (10 g), H2O (40 ml), HOAc (8 ml) and Bu2O (8 ml) was heated at 80°-100° C. for 2.5 h, allowed to cool and filtered. The solid was thoroughly extracted with Et2O and the extract was dried (Na2SO4), treated with carbon and concentrated to an oil. Extraction of the latter with pet ether and cooling the extract gave 2.2 g (66%) of 8-amino-6-methoxy-4-methyl-5-(4-phenylbutoxy)quinoline as yellow-green crystals, mp 59°-59.5° C. Recrystallization from pet ether afforded the analytical sample as yellow crystals, mp 60°-61° C.

Workup

  1. temperaturewas heated at 80°-100° C. for 2.5 h
  2. temperatureto cool
  3. filtrationfiltered
  4. extractionThe solid was thoroughly extracted with Et2O
  5. dry with materialthe extract was dried (Na2SO4)
  6. additiontreated with carbon
  7. concentrationconcentrated to an oil
  8. extractionExtraction of the latter with pet ether
  9. temperaturecooling the extract

Sources & evidence

ORD record
ord-673f54b4627e4c19b765cf0ca42f0244
Source dataset
uspto-grants-1992_04
Patent number
US05104885

Reaction notes

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