Ammonia → 2-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxamide

HRID 1870735Notes

Reaction equation

HRID 1870735 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17](O)=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10].C(C1NC=CN=1)(C1[NH:25]C=CN=1)=O.N>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([NH2:25])=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 226225362-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxylic Acid

Product 1

HCID 183577602-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxamideYield 108.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxylic acid (example 7) (1.8 g, 5.1 mmol) in tetrahydrofuran (40 ml) treated with carbonyl diimidazole (1.8 g, 11 mmol) and heated at gentle reflux for 4 hours. The mixture was cooled and added to 0.88 aqueous ammonia solution (60 ml), stirred for 1 hour at ambient temperature and then evaporated to low bulk. The resultant white solid was diluted with ice/water, filtered, washed with cold water and air dried to give the title compound as a white solid (1.93 g, 100%).

Workup

  1. temperatureheated
  2. temperatureat gentle reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. customevaporated to low bulk
  5. additionThe resultant white solid was diluted with ice/water
  6. filtrationfiltered
  7. washwashed with cold water and air
  8. customdried

Sources & evidence

ORD record
ord-5d36bb5c77764b9db24abb3dde4d9cda
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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