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

HRID 1111393Notes

Reaction equation

HRID 1111393 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][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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 543454366-Methoxy-4-methyl-8-nitro-5-(8-phenyloctoxy) quinoline

Product 1

HCID 543948298-Amino-6-methoxy-4-methyl-5-(8-phenyloctoxy) quinolineYield 61.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 6-methoxy-4-methyl-8-nitro-5-(8-phenyloctoxy) quinoline (2.1 g, 0.005 mol), degreased 40 mesh Fe filings (5 g), H2O (20 ml), HOAc (4 ml) and n-Bu2O (4 ml) was heated at 80° C. to 1.5 h, cooled and filtered. The solid was thoroughly extracted with Et2O and the filtered extract was dried (Na2SO4), treated with carbon and concentrated to an oil. Trituration with pet ether gave 1.2 g (61%) of 8-amino-6-methoxy-4-methyl-5-(8-phenyloctoxy) quinoline as yellow-green solid, mp 33°-34° C. Crystallization from pet ether (Darco) gave the analytical sample as yellow green crystals, mp 39°-40° C.

Workup

  1. temperaturewas heated at 80° C. to 1.5 h
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionThe solid was thoroughly extracted with Et2O
  5. extractionthe filtered extract
  6. dry with materialwas dried (Na2SO4)
  7. additiontreated with carbon
  8. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-e1e3b54f1b014628bc2b82556250e010
Source dataset
uspto-grants-1990_12
Patent number
US04980360

Reaction notes

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