Methanol → HCID 13314808, compound

HRID 325798Notes

Reaction equation

HRID 325798 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1.CO.[H][H]>[C].[Pd].C(OCC)(=O)C>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 128308312-Methyl-6-[2-(4-nitrophenoxy)ethyl]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 13314808HCID 13314808, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.8 g of 4-[2-(6-methyl-2-pyridyl)ethoxy]nitrobenzene in the mixture consisting of 30 ml of methanol and 20 ml of ethyl acetate is added 0.5 g of 10% palladium carbon, and then the mixture is shaken in a stream of hydrogen. After absorption of hydrogen ceased, the mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is dissolved in ethyl acetate and washed with water, dried over anhydrous magnesium sulfate and then concentrated to give 2.24 g of 4-[2-(6-methyl-2-pyridyl)ethoxy]aniline as yellowish brown powder.

Workup

  1. customAfter absorption of hydrogen
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fb10899b0d3741a681b970bc8c015071
Source dataset
uspto-grants-1984_04
Patent number
US04443246

Reaction notes

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