Acetic Anhydride → HCID 58674419, compound

HRID 1994147Notes

Reaction equation

HRID 1994147 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 58674489HCID 58674489, compound

Product 1

HCID 58674419HCID 58674419, compoundYield 772.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-{3-[(2-aminopyridin-4-yl)oxy]phenyl}propanoate (390 mg, 0.14 mmol) was dissolved in pyridine (5 mL) and the reaction mixture was cooled at 0° C. and stirred for 1 h. Acetic anhydride (135 μL, 0.14 mmol) was added dropwise and the reaction mixture was allowed to stir for 1 h. The reaction mixture was allowed to warm to rt and to stir overnight. The reaction was quenched with water and extracted with EtOAc. The organic solutions were dried (MgSO4), filtered and concentrated. The residue was purified column chromatography to give the title compound (340 mg, 76%) as a white solid. LCMS: (FA) ES+ 315.29 (M+1).

Workup

  1. stirringto stir for 1 h
  2. temperatureto warm to rt
  3. stirringto stir overnight
  4. customThe reaction was quenched with water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic solutions were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified column chromatography

Sources & evidence

ORD record
ord-8a8e67775dfb4e49ab95d9c6bbd4b0a3
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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