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

HRID 1030183
Notes
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Reaction equation

HRID 1030183 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8909Butyl etherHCID 198221476-Methoxy-4-methyl-5-(5-phenylpentoxy)-8-nitroquinoline

Product 1

HCID 198221428-Amino-6-methoxy-4-methyl-5-(5-phenylpentoxy)quinolineYield 87%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst
HCID 962
Water
Solvent
2×

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

  1. temperaturecooled
  2. filtrationfiltered
  3. extractionThe dark solid was thoroughly extracted with warm Et2O (total, Ca. 500 ml)
  4. dry with materialthe extract was dried (Na2SO4)
  5. additiontreated with charcoal
  6. concentrationconcentrated
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes