Sodium Carbonate → 2-(6-Methylpyridin-2-yl)ethan-1-amine

HRID 1110922Notes

Reaction equation

HRID 1110922 reaction equation
O.NN.[CH3:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][N:13]2C(=O)C3=CC=CC=C3C2=O)[CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][NH2:13])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 14478208N-[2-(6-methyl-2-pyridyl)ethyl]phthalimide

Product 1

HCID 15141652-(6-Methylpyridin-2-yl)ethan-1-amineYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

28.5 ml (29.4 g, 586 mmol) of hydrazine monohydrate was added to a solution of 39.0 g (147 mmol) of N-[2-(6-methyl-2-pyridyl)ethyl]phthalimide obtained in the above step (1) in 300 ml of ethanol and the mixture was stirred at room temperature for 1.5 h. The mixture was poured into 300 ml of a saturated aqueous sodium carbonate solution. After extraction with chloroform, the organic layer was concentrated and the oily residue thus obtained was purified by distillation (75° to 80° C./0.01 mmHg). 12.6 g (yield: 63%) of the intended compound was obtained as a colorless oil.

Workup

  1. extractionAfter extraction with chloroform
  2. concentrationthe organic layer was concentrated
  3. customthe oily residue thus obtained
  4. distillationwas purified by distillation (75° to 80° C./0.01 mmHg)

Sources & evidence

ORD record
ord-dbfd47f4fb354dd7847f27eca00808bf
Source dataset
uspto-grants-1990_12
Patent number
US04977165

Reaction notes

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