Putrescine → N-(2-aminophenyl)-6-(4-aminobutylamino)nicotinamide

HRID 1695035Notes

Reaction equation

HRID 1695035 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]([NH2:23])[CH2:19][CH2:20][CH2:21][NH2:22]>>[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:22][CH2:21][CH2:20][CH2:19][CH2:18][NH2:23])=[N:12][CH:11]=1

Participants

3

Reactant 2

HCID 1045PutrescineHCID 22478760N-(2-aminophenyl)-6-chloronicotinamide

Product 1

HCID 57993720N-(2-aminophenyl)-6-(4-aminobutylamino)nicotinamideYield 53%

Procedure

N-(2-Aminophenyl)-6-chloronicotinamide (248 mg, 1 mmol) and 7 ml of 1,4-butanediamine were heated to 80° C. for 3 hours. The excess 1,4-butanediamine 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 (158 mg, 53% yield) as a brown solid. LC-MS (m/z) 300 (M+1).

Workup

  1. customThe excess 1,4-butanediamine 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-fb671f46b72c446a918b649aad55f9cd
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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