Acetic Anhydride → HCID 10397459, compound

HRID 1620269Notes

Reaction equation

HRID 1620269 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].CCN(C(C)C)C(C)C.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:20](=[O:22])[CH3:21])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 5811103-Fluoro-4-methoxyaniline

Product 1

HCID 10397459HCID 10397459, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluoro-4-methoxyaniline (1.15 g, 8.15 mmol) in dry CH2Cl2 (81 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer were added DIEA (5.4 mL, 32.7 mmol), DMAP (221 mg, 1.81 mmol) and acetic anhydride (4.4 mL, 46.5 mmol) and the mixture was stirred overnight at RT. The solution was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50) gave N-(3-fluoro-4-methoxyphenyl)acetamide SMA 44032 as a brown solid (1.08 g, 72% yield).

Workup

  1. washThe solution was washed with brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated at 40° C. under vacuum
  5. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50)

Sources & evidence

ORD record
ord-160be16268e54a1dbe9c96d3954f72f7
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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