Pyridine → 2-(2-Methoxyphenyl)acetamide

HRID 2215180Notes

Reaction equation

HRID 2215180 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O.[N:13]1C=CC=CC=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)([O-])O.[NH4+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([NH2:13])=[O:12]

Participants

6

Procedure

2-Methoxyphenylacetic acid (10.0 g, 60.1 mmol) was dissolved in acetonitrile (15 mL). Subsequently, pyridine (2.84 g, 36.1 mmol) and di-tert-butyl dicarbonate [Boc2O (19.6 g, 90.2 mmol)] were added thereto. The mixture was stirred for 10 minutes at room temperature, and then ammonium hydrogencarbonate (7.1 g, 90.2 mmol) were added. After completion of reaction, the reaction mixture was concentrated under reduced pressure. Thereafter, the resultant concentrate was added to water, and the resultant mixture was extracted with chloroform, followed by washing sequentially with 1M hydrochloric acid and brine. The resultant mixture was subjected to drying over magnesium sulfate and concentration under reduced pressure. The resultant concentrate was used in Production Example 18 without purification.

Workup

  1. customAfter completion of reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. concentrationThereafter, the resultant concentrate
  4. additionwas added to water
  5. extractionthe resultant mixture was extracted with chloroform
  6. washby washing sequentially with 1M hydrochloric acid and brine
  7. dry with materialto drying over magnesium sulfate and concentration under reduced pressure
  8. concentrationThe resultant concentrate
  9. customwas used in Production Example 18 without purification

Sources & evidence

ORD record
ord-477cfcc0c86949cfa3e8f1f7d3c129e8
Source dataset
uspto-grants-2006_09
Patent number
US07109226B2

Reaction notes

Loading…