Ethylenediamine → N~1~-(7-Chloroquinolin-4-yl)ethane-1,2-diamine

HRID 497355Notes

Reaction equation

HRID 497355 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:13][CH2:14][CH2:15][NH2:16]>>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:13][CH2:14][CH2:15][NH2:16])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 68664,7-Dichloroquinoline

Product 1

HCID 221208N~1~-(7-Chloroquinolin-4-yl)ethane-1,2-diamine

Conditions

Temperature
85 °C

Procedure

A mixture of 4,7-dichloroquinoline (2.0 g, 10 mmol) and 1,2-diaminoethane (2.7 g, 45 mmol) is heated at 85° C. for 5 hours with magnetic stirring. After adding 1N soda (15 ml), the solid obtained is extracted with ethyl acetate (100 ml) at 50° C. The organic phase is washed with distilled water and then using a saturated NaCl solution and then again with distilled water and finally is dried on sodium sulphate. The solvent is evaporated and the product obtained is vacuum-dried (1.3 g, 58%).

Workup

  1. additionAfter adding 1N soda (15 ml)
  2. customthe solid obtained
  3. extractionis extracted with ethyl acetate (100 ml) at 50° C
  4. washThe organic phase is washed with distilled water
  5. dry with materialagain with distilled water and finally is dried on sodium sulphate
  6. customThe solvent is evaporated
  7. customthe product obtained
  8. customis vacuum-dried (1.3 g, 58%)

Sources & evidence

ORD record
ord-ac06ff2e5162486284e69edc6d27050c
Source dataset
uspto-grants-2005_09
Patent number
US06949569B2

Reaction notes

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