Acetic Acid → 8-Amino-6-methoxy-4-methyl-5-(5-phenylpentoxy)quinoline

HRID 1111386Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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].CC(O)=O.O(CCCC)CCCC>O.[Fe]>[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][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[C:6]2[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred mixture of 6-methoxy-4-methyl-5-(5-phenylpentoxy)-8-nitroquinoline (9.0 g, 0.024 mole), degreased 40 mesh Fe filings (22.5 g), H2O (90 ml), HOAc (18 ml) and Bu2O (18 ml) was heated at 80° C. for 1 h, cooled, diluted with H2O and filtered. The dark solid was thoroughly extracted with warm Et2O (total, Ca. 500 ml) and the extract was dried (Na2SO4), treated with charcoal and concentrated. The resulting dark brown oil was crystallized from pet ether to give 7.3 g (87%) of 8-Amino-6-methoxy-4-methyl-5-(5-phenylpentoxy) quinoline as yellow green crystals, mp 65°-66° C. This material was used without further purification.

Workup

temperaturecooled
filtrationfiltered
extractionThe dark solid was thoroughly extracted with warm Et2O (total, Ca. 500 ml)
dry with materialthe extract was dried (Na2SO4)
additiontreated with charcoal
concentrationconcentrated
customThe resulting dark brown oil was crystallized from pet ether

Sources & evidence

ORD record: ord-841bb4138eb940f887ba628a2f6ccde6
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04980360

Reaction notes

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