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Pyridine → 2-(2-Methoxyphenyl)acetamide

HRID 350835
Notes
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Reaction equation

HRID 350835 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 71342-Methoxyphenylacetic acidHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 806622-(2-Methoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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-19e63721000f4f039d20040447f1d817
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07183295B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes