1,2-Dichloroethane → 2-Methyl-N-(propan-2-yl)pyridine-3-carboxamide

HRID 1094459Notes

Reaction equation

HRID 1094459 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C1C=C[C:14]2N(O)N=[N:17][C:15]=2[CH:16]=1.C(N)(C)C.C(N(CC)CC)C.C(Cl)CCl>CN(C=O)C>[CH:15]([NH:17][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[CH3:1])([CH3:16])[CH3:14]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6363IsopropylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 6433732-Methylnicotinic acid

Product 1

HCID 597998332-Methyl-N-(propan-2-yl)pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl nicotinic acid (2.5 g, 18 mmol), HOBT (3.7 g, 27 mmol), isopropylamine (3.1 mL, 36 mmol), and triethylamine (7.5 mL, 54 mmol) in 150 mL of DMF is added EDC (5.2 g, 27 mmol). The reaction is allowed to stir at room temperature for 24 hours and is then concentrated under reduced pressure. Ethyl acetate and brine is added and the layers are separated. The organic layer is dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification of the crude residue by silica gel flash column chromatography gives the title compound.

Workup

  1. concentrationis then concentrated under reduced pressure
  2. additionEthyl acetate and brine is added
  3. customthe layers are separated
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the crude residue by silica gel flash column chromatography

Sources & evidence

ORD record
ord-509b6fe0b0124337a5a01064337400f3
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

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