Isobutyryl chloride → HCID 66667875, compound

HRID 512051Notes

Reaction equation

HRID 512051 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1.C(N(C(C)C)C(C)C)C.[C:23](Cl)(=[O:27])[CH:24]([CH3:26])[CH3:25]>C(Cl)Cl>[C:23]([NH:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1)(=[O:27])[CH:24]([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 66667743Methyl 6-(aminomethyl)pyridine-3-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 66667875HCID 66667875, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold suspension of methyl 6-(aminomethyl)nicotinate hydrochloride (1.00 g, 4.18 mmol) and N-ethyl-N-isopropylpropan-2-amine (1.89 g, 2.55 mL, 14.6 mmol) in DCM (10 mL) was added dropwise a solution of isobutyryl chloride (535 mg, 526 μL, 5.02 mmol) in DCM (3 mL). The reaction mixture was allowed to warm to room temperature, washed with water (5 mL), 10% aqueous citric acid solution (5 mL), saturated aqueous sodium bicarbonate solution (5 mL), brine (5 mL), dried over magnesium sulfate, filtered and evaporated to yield the title compound as a pale orange solid (0.988 g, 100%):

Workup

  1. washwashed with water (5 mL), 10% aqueous citric acid solution (5 mL), saturated aqueous sodium bicarbonate solution (5 mL), brine (5 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-2d8b380a67f440118d7968744c783445
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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