Ethylenediamine → N-(2-aminophenyl)-6-(2-aminoethylamino)nicotinamide

HRID 1695029Notes

Reaction equation

HRID 1695029 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13](Cl)=[N:12][CH:11]=1.[CH2:18]([NH2:21])[CH2:19][NH2:20]>>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([NH:20][CH2:19][CH2:18][NH2:21])=[N:12][CH:11]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 22478760N-(2-aminophenyl)-6-chloronicotinamide

Product 1

HCID 57993739N-(2-aminophenyl)-6-(2-aminoethylamino)nicotinamideYield 55%

Procedure

N-(2-Aminophenyl)-6-chloronicotinamide (248 mg, 1 mmol) and 5 ml of ethylenediamine were heated to 80° C. for 3 hours. The excess ethylenediamine was removed under vacuum. To the residue was added 5 ml of 0.20 M NaOH. The mixture was extracted with 100 ml of ethyl acetate. The ethyl acetate was removed under vacuum to give the title compound (150 mg, 55% yield) as a brown solid. LC-MS (m/z) 272 (M+1).

Workup

  1. customThe excess ethylenediamine was removed under vacuum
  2. additionTo the residue was added 5 ml of 0.20 M NaOH
  3. extractionThe mixture was extracted with 100 ml of ethyl acetate
  4. customThe ethyl acetate was removed under vacuum

Sources & evidence

ORD record
ord-dab637f7d65849f6aa4da74276418162
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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