1,2-Dichloroethane → 2-Amino-5-bromo-N-(2-hydroxyethyl)nicotinamide

HRID 1761062Notes

Reaction equation

HRID 1761062 reaction equation
C(Cl)CCl.[NH2:5][C:6]1[N:14]=[CH:13][C:12]([Br:15])=[CH:11][C:7]=1[C:8]([OH:10])=O.[CH2:16]([CH2:18][NH2:19])[OH:17].C1C=CC2N(O)N=NC=2C=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[NH2:5][C:6]1[N:14]=[CH:13][C:12]([Br:15])=[CH:11][C:7]=1[C:8]([NH:19][CH2:18][CH2:16][OH:17])=[O:10]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 7374452-Amino-5-bromonicotinic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 225937682-Amino-5-bromo-N-(2-hydroxyethyl)nicotinamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDC (2.91 g, 15.2 mmole) was added to a solution 2-amino5-bromonicotinic acid (3.00 g, 13.8 mmole), ethanolamine (0.93 g, 15.2 mmole), HOBt H2O (2.05 g, 15.2 mmole), and diisopropylethylamine (2.64 mL, 15.2 mmole) in DMF (50 mL) at RT and the reaction solution was stirred overnight. The reaction contents were poured into H2O (200 mL) and the resulting mixture was extracted with EtOAc (2×200 mL). The combined organic extracts were washed with H2O and brine and then dried over Na2SO4. Concentration of the organic extracts afforded the title compound as a yellow solid which was used without further purification: MS (ES) m/e 261 (M+H)+.

Workup

  1. customThe reaction contents
  2. extractionthe resulting mixture was extracted with EtOAc (2×200 mL)
  3. washThe combined organic extracts were washed with H2O and brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-cea1dff512e44d24bae6b4fe736cb71a
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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