Hydrazine hydrate (1:1) → 8-Quinolinamine, 4-methyl-

HRID 613452Notes

Reaction equation

HRID 613452 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[CH3:14])([O-])=O.O.NN>CO>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[CH3:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 760484-Methyl-8-nitroquinoline

Product 1

HCID 973748-Quinolinamine, 4-methyl-Yield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 8-nitro-4-methylquinoline (250 mg), ferric chloride hexahydrate (7.18 mg) and activated carbon (38 mg) in methanol was added hydrazine monohydrate (266 mg) at 65° C., and the mixture was stirred for 1 hour at the same temperature. Insoluble material was filtered off, and the filtrate was concentrated in vacuo The mixture was dissolved in ethyl acetate, washed with brine, dried over magnesium sulfate and evaporated in vacuo to give 8-amino-4-methylquinoline (208.8 mg).

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo The mixture
  3. dissolutionwas dissolved in ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4e283a1864e24db3b7cce1dfcce08f96
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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