Water → Pyridine-2-carboxylic acid (2-acetyl-5-methoxy-phenyl)-amide

HRID 1815716Notes

Reaction equation

HRID 1815716 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[NH2:10][C:11]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:12]=1[C:13]([C:15]1C=CC=CC=1)=[O:14].O=P(Cl)(Cl)Cl.O>N1C=CC=CC=1>[C:13]([C:12]1[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:11]=1[NH:10][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9])(=[O:14])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 1018Picolinic acidHCID 24813Phosphorus oxychlorideHCID 254180(2-Amino-4-methoxyphenyl)(phenyl)methanone

Product 1

HCID 20773657Pyridine-2-carboxylic acid (2-acetyl-5-methoxy-phenyl)-amideYield 93.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 2-picolic acid (3.73 g, 30.3 mmol) and 2-amino-4-methoxybenzophenone (5.0 g, 30.3 mmol) at −30° C. dissolved in pyridine (150 mL) was added POCl3 (3.7 mL, 45.4 mmol) in 5 min. the reaction mixture was stirred for 3 hr at the temperature, and stirred at rt overnite. The reaction mixture was poured into cold water and extracted with EtOAc (3×). The combined extract was dried to provide the product (7.67 g, 93%): 1H NMR (methanol-d4) δ ppm 2.65 (s, 3H), 3.92 (s, 3H), 6.78 (m, 1H), 7.60 (m, 1H), 8.00 (m, 1H), 8.06 (m, 1H), 8.21 (d, J=7.63 Hz, 1H), 8.59 (t, J=2.29 Hz, 1H), 8.76 (d, J=3.97 Hz, 1H). LC-MS (retention time: 1.56, Method D), MS m/z 271 (M++1).

Workup

  1. stirringstirred at rt overnite
  2. extractionextracted with EtOAc (3×)
  3. extractionThe combined extract
  4. customwas dried

Sources & evidence

ORD record
ord-4910964d8aa949769117dd8d784eb425
Source dataset
uspto-grants-2005_04
Patent number
US06878722B2

Reaction notes

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