Acetic Acid → 6-Chloro-4-(thiophen-2-ylmethylamino)nicotinamide

HRID 513278Notes

Reaction equation

HRID 513278 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.C([NH2:22])=O.CC[O-].[Na+].CC(O)=O>CN(C=O)C.CCO.O>[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[C:5]([C:6]([NH2:22])=[O:7])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 713FormamideHCID 2723922Sodium ethoxide2×HCID 86664545Ethyl 6-chloro-4-(thiophen-2-ylmethylamino)nicotinate

Product 1

HCID 584398316-Chloro-4-(thiophen-2-ylmethylamino)nicotinamideYield 79.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 6-chloro-4-(thiophen-2-ylmethylamino)nicotinate (1.54 g, 5.19 mmol) in DMF (8 mL) and HCONH2 (2 mL, 50.3 mmol), NaOEt (21% by wt., 7.80 mL, 20.9 mmol) in EtOH was added. The mixture was stirred at room temperature for 20 min. HOAc (2 mL) was added to neutralize NaOEt. Water was then added to induce precipitation. The precipitate was collected, dried on vacuum to give 6-chloro-4-(thiophen-2-ylmethylamino)nicotinamide as a solid (1.10 g).

Workup

  1. customprecipitation
  2. customThe precipitate was collected
  3. customdried on vacuum

Sources & evidence

ORD record
ord-708b26475f07488aa45eb68d998c2a85
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

Loading…