4-Methoxyphenol → 6-Methoxy-5-[4-methoxyphenoxy]-8-nitrolepidine

HRID 1388572Notes

Reaction equation

HRID 1388572 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[OH-].[K+].[CH3:12][C:13]1[C:22]2[C:17](=[C:18]([N+:26]([O-:28])=[O:27])[CH:19]=[C:20]([O:24][CH3:25])[C:21]=2Cl)[N:16]=[CH:15][CH:14]=1.C(O)(=O)CCC(O)=O.NCCCC(NC1C=C(OC)C(OC2C=CC=C(C(F)(F)F)C=2)=C2C=1N=CC=C2C)C>C(OCCO)C.O>[CH3:25][O:24][C:20]1[C:21]([O:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[C:22]2[C:17](=[C:18]([N+:26]([O-:28])=[O:27])[CH:19]=1)[N:16]=[CH:15][CH:14]=[C:13]2[CH3:12]

Participants

7

Reactant 4

HCID 90154-MethoxyphenolHCID 14797Potassium HydroxideHCID 30619681,4-Pentanediamine, N(sup 4)-(6-methoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-, butanedioate (1:1)HCID 120499275-Chloro-6-methoxy-4-methyl-8-nitroquinoline

Product 1

HCID 6309586-Methoxy-5-[4-methoxyphenoxy]-8-nitrolepidineYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 4-methoxyphenol (5.76 g, 46.5 mmol) and KOH (2.61 g, 46.6 mmol) in 2-ethoxyethanol (90 mL) was heated with removal of water until the pot temperature reached 130° after which time 4-methyl-5-chloro-6-methoxy-8-nitroquinoline, prepared as in Example 1 (9 g, 35.7 mmol), was added. The reaction mixture was heated at reflux (130°) for 2 hours and cooled at 5° for 18 hours. Filtration afforded the title compound (8.25 g, 68%), mp 158°-60°.

Workup

  1. customreached 130°
  2. additionwas added
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux (130°) for 2 hours
  5. temperaturecooled at 5° for 18 hours
  6. filtrationFiltration

Sources & evidence

ORD record
ord-5dc77f9349f043879ec78cfdc25e9504
Source dataset
uspto-grants-1984_02
Patent number
US04431807

Reaction notes

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