Ethylenediamine → HCID 57993737, compound

HRID 1695056Notes

Reaction equation

HRID 1695056 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15](Cl)=[N:14][CH:13]=1.[CH2:20]([NH2:23])[CH2:21][NH2:22]>>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([NH:22][CH2:21][CH2:20][NH2:23])=[N:14][CH:13]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 57993731HCID 57993731, compound

Product 1

HCID 57993737HCID 57993737, compoundYield 48%

Procedure

N-(2-Amino-4-methoxyphenyl)-6-chloronicotinamide (277 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 (144 mg, 48% yield) as a brown solid. LC-MS (m/z) 302 (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-e56685ec6a0b47da8849647589b6d12d
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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