Toluene → HCID 605233, compound

HRID 1863105Notes

Reaction equation

HRID 1863105 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][O:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[C:11]([N+:20]([O-])=O)[CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.O.NN>[Ni].C(O)C>[NH2:20][C:11]1[CH:12]=[C:13]([O:18][CH3:19])[CH:14]=[C:15]2[C:10]=1[N:9]=[C:8]([O:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:24][CH:23]=1)[CH:17]=[CH:16]2

Participants

6

Reactant 3

HCID 1140TolueneHCID 24654Hydrazine hydrate (1:1)HCID 580807HCID 580807, compound

Product 1

HCID 605233HCID 605233, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The foregoing nitro compound (34.48 g, 0.1 mole), 500 ml of a 1:1 mixture (v/v) of toluene and ethanol, 10 g wet Raney nickel, and 50 ml 85% hydrazine hydrate was refluxed for 6 hr. Thereafter, the condenser was placed for distillation and heated until vapors at the still-head were alkaline. A small amount of hydroquinone was added, and the hot mixture filtered. The filtrates were concentrated in vacuo, leached with a little warm ethanol, then crystallized from ethanol (charcoal). The 8-amino-2-(4-chlorobenzyloxy)-6-methoxyquinoline was obtained in 97% yield; mp 123.5°-125°.

Workup

  1. distillationThereafter, the condenser was placed for distillation
  2. temperatureheated until vapors at the
  3. additionA small amount of hydroquinone was added
  4. filtrationthe hot mixture filtered
  5. concentrationThe filtrates were concentrated in vacuo
  6. temperaturea little warm ethanol
  7. customcrystallized from ethanol (charcoal)

Sources & evidence

ORD record
ord-74e153f6840f4cdbad9c2588e0faef28
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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