HCID 19876796, compound → 1,2-Ethanediamine, N-2-quinolinyl-

HRID 1886044Notes

Reaction equation

HRID 1886044 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][CH2:12][CH2:13][NH:14]C(=O)C>Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][CH2:12][CH2:13][NH2:14]

Participants

3

Reactant 1

HCID 19876796HCID 19876796, compound

Product 1

HCID 105355881,2-Ethanediamine, N-2-quinolinyl-Yield 69.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-[2-[(quinolin-2-yl)amino]ethyl]acetamide (6.8 g, 0.030 mol) in 2N HCl (45 ml, 0.090 ml) was heated under reflux for 20 hours. The solution was cooled and extracted with EtOAc. The aqueous phase was made basic (pH9) with solid KOH, saturated with NaCl, and extracted with EtOAc. The combined extracts were dried (MgSO4) and concentrated to give 3.89 g (68%) of an off-white solid m.p. 124°-125° C.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperatureThe solution was cooled
  3. extractionextracted with EtOAc
  4. extractionsaturated with NaCl, and extracted with EtOAc
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8d4e3c17bbda42e5a06a8db5eacf995f
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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