Water → 4-(Quinolin-2-ylmethoxy)aniline

HRID 727806

Reaction equation

HRID 727806 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN.O>CO.O1CCCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 137703602-[(4-Nitrophenoxy)methyl]quinoline

Product 1

HCID 27475694-(Quinolin-2-ylmethoxy)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

117.8 g (0.42 mol) of 2-(4-nitrophenoxymethyl)quinoline were dissolved in 1 l of methanol/tetrahydrofuran (1:1). About 5 g of Raney nickel were then added and the mixture was warmed to 35° C. 63.1 g (1.26 mol) of hydrazine hydrate ×H2O were then added dropwise and the mixture was stirred overnight. The residue was filtered off, the solution was concentrated in vacuo and the residue was taken up with methylene chloride. The mixture was then washed with water and conc. hydrochloric acid was added to the organic phase. The precipitate deposited was filtered off, washed with 2 N hydrochloric acid, dissolved in water and rendered alkaline with 20% strength NaOH. The residue was dried in vacuo.

Workup

  1. filtrationThe residue was filtered off
  2. concentrationthe solution was concentrated in vacuo
  3. washThe mixture was then washed with water and conc. hydrochloric acid
  4. additionwas added to the organic phase
  5. filtrationThe precipitate deposited was filtered off
  6. washwashed with 2 N hydrochloric acid
  7. dissolutiondissolved in water
  8. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-ed44bba192c04457973ed487570d6496
Source dataset
uspto-grants-1991_09
Patent number
US05045547

Linked notes

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