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

HRID 1030183Notes

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-f911f577630c488695a1e83fdba13857
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05104885

Reaction notes

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