Hydrochloric Acid → 5-Ethylpyridin-2-amine

HRID 1740967Notes

Reaction equation

HRID 1740967 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2C(=O)C3C=CC=CC=3OC2(C)C)=[N:7][CH:8]=1)[CH3:2].Cl>>[NH2:9][C:6]1[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 218344093-(5-ethyl-2-pyridinyl)-2,2-dimethyl-2,3-dihydro-(4H)-1,3-benzoxazin-4-one

Product 1

HCID 98127775-Ethylpyridin-2-amineYield 84%

Procedure

Following the general method of K. Wachi and A. Terada (Chem. Pharm. Bull., 1980, 28, 465-472), a mixture 81 mg (0.29 mmoles) of 3-(5-ethyl-2-pyridinyl)-2,2-dimethyl-2.3-dihydro-(4H)-1,3-benzoxazin-4-one and 2.0 mL of concentrated hydrochloric acid was heated to reflux for 8 h. The reaction was cooled to room temperature and the solvent was evaporated. The residue was dissolved in 4 mL ethyl acetate and washed with 3×1 mL of a 1:1 mixture of 10% of aqueous sodium hydroxide solution and saturated aqueous sodium chloride. The organic solution was dried (sodium sulfate), decanted, and evaporated to give 26 mg (84% yield) of 2-amino-5-ethylpyridine as an amber oil.

Workup

  1. temperatureto reflux for 8 h
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in 4 mL ethyl acetate
  4. washwashed with 3×1 mL of a 1:1 mixture of 10% of aqueous sodium hydroxide solution and saturated aqueous sodium chloride
  5. dry with materialThe organic solution was dried (sodium sulfate)
  6. customdecanted
  7. customevaporated

Sources & evidence

ORD record
ord-6d5f58fbb0e04d3c97eeeca34a33337e
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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