Water → 2-Acetyl-6-(methoxycarbonyl)phenyl isonicotinate

HRID 876546Notes

Reaction equation

HRID 876546 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[C:10]([C:13]1[C:14]([OH:23])=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])(=[O:12])[CH3:11].CCN(C(C)C)C(C)C.O>CC#N>[C:7]([O:23][C:14]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=[CH:22][C:13]=1[C:10](=[O:12])[CH3:11])(=[O:8])[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 417436Pyridine-4-carbonyl chlorideHCID 13037297Methyl 3-acetyl-2-hydroxybenzoate

Product 1

HCID 584772802-Acetyl-6-(methoxycarbonyl)phenyl isonicotinateYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyridine-4-carbonyl chloride 42 (705 mg, 5 mmol) was added to a solution of methyl 3-acetyl-2-hydroxybenzoate 38 (650 mg, 3.6 mmol) and DIEA (932 mg, 7.2 mmol) in CH3CN (10 mL). The reaction mixture was stirred at room temperature for 12 h, poured into H2O (20 mL) and extracted with CH2Cl2. The combined organic extracts were dried (MgSO4) and concentrated. The residue was purified by prep HPLC to give the product as a yellow solid (855 mg, 83% yield).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-90e11da531a446d8b0a1d65849f24528
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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