4-Isopropylaniline → 6-chloro-N-(4-propan-2-ylphenyl)pyridine-3-carboxamide

HRID 218544Notes

Reaction equation

HRID 218544 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH:11]([C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)([CH3:13])[CH3:12].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(N(CC)CC)C>[CH:11]([C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:6]([C:5]2[CH:4]=[N:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[O:8])=[CH:16][CH:15]=1)([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 74644-IsopropylanilineHCID 792226-Chloronicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 24739216-chloro-N-(4-propan-2-ylphenyl)pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

6-Chloronicotinic acid (3.15 g), 4-isopropylaniline (2.73 mL) and triethylamine (5.6 mL) were dissolved in DMF (150 mL). 1-Hydroxybenzotriazole monohydrate (hereinafter to be abbreviated as HOBt.H2O) (3.22 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (hereinafter to be abbreviated as WSCI.HCl) (4.03 g) were added under ice-cooling. The mixture was stirred at room temperature for one day and the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and ether was added to the residue. The precipitated solid was collected by filtration to give N-(4-isopropylphenyl)-6-chloropyridine-3-carboxamide (4.72 g).

Workup

  1. temperaturecooling
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. additionether was added to the residue
  7. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-2546f866d3654c7585b7867b894926cc
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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