1,2-Dichloroethane → 4-bromo-N-(2-hydroxyethyl)picolinamide

HRID 58060

Reaction equation

HRID 58060 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.[NH2:11][CH2:12][CH2:13][OH:14].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(C(C)C)C(C)C)C>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:11][CH2:12][CH2:13][OH:14])=[O:10])[CH:3]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7351504-Bromopyridine-2-carboxylic acid

Product 1

HCID 897817404-bromo-N-(2-hydroxyethyl)picolinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 4-bromopicolinic acid (0.3 g, 1.485 mmol) in DMF (4 mL) were added 2-aminoethanol (0.181 g, 2.97 mmol), HOBt (0.301 g, 2.228 mmol), and EDC (0.456 g, 2.376 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (1.293 mL, 7.43 mmol). The reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was diluted with DCM, washed with brine, and concentrated to give the title compound, which was used without further purification.

Workup

  1. washwashed with brine
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7c297db1e83246e1a0f83a2fd9b37419
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Linked notes

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