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Butyl ether → 8-Amino-6-methoxy-4-methyl-5-(9-phenylnonoxy) quinoline

HRID 1111395
Notes
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Reaction equation

HRID 1111395 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][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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(CCCC)CCCC>[Fe].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][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[C:6]2[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8909Butyl etherHCID 540302836-Methoxy-4-methyl-8-nitro-5-(9-phenylnonoxy) quinoline

Product 1

HCID 541929178-Amino-6-methoxy-4-methyl-5-(9-phenylnonoxy) quinolineYield 64%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 6-methoxy-4-methyl-8nitro-5-(9-phenylnonoxy) quinoline (11 g, 0.025 mol), degreased 40 mesh Fe filings (30 g), H2O (100 ml), HOA c (20 ml) and n-Bu2O (20 ml) was heated at 80° C. for 2 h, cooled and filtered. The solid residue and the filtrate were thoroughly extracted with warm Et2O and the combined extracts were dried (Na2SO4), treated with Darco, and concentrated. The resulting solid was dissolved in pet ether (Darco) and cooled in dry ice--Me2CO to give 6.5 g (64) of 8-amino-6-methoxy-4-methyl-5-(9-phenylnonoxy) quinoline as pale yellow crystals, mp 32°-32.5° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. extractionThe solid residue and the filtrate were thoroughly extracted with warm Et2O
  4. dry with materialthe combined extracts were dried (Na2SO4)
  5. additiontreated with Darco
  6. concentrationconcentrated
  7. dissolutionThe resulting solid was dissolved in pet ether (Darco)
  8. temperaturecooled in dry ice

Sources & evidence

ORD record
ord-587fb22c925d4085888c5f2894b92867
Source dataset
uspto-grants-1990_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04980360

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes