Water → N-(7-Cyano-2,3-dihydrobenzofuran-4-yl)-acetamide

HRID 751036Notes

Reaction equation

HRID 751036 reaction equation
[C:1]([NH:4][C:5]1[C:10]2[CH2:11][CH2:12][O:13][C:9]=2[C:8]([C:14]([NH2:16])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C1COCC1>[C:14]([C:8]1[C:9]2[O:13][CH2:12][CH2:11][C:10]=2[C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1)#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 684594094-Acetylamino-2,3-dihydrobenzofuran-7-carboxylic acid amide

Product 1

HCID 68459223N-(7-Cyano-2,3-dihydrobenzofuran-4-yl)-acetamideYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of compound 4A (3.5 g, 16 mmol) in THF (64 mL) at 0° C. under Ar was added pyridine (6.5 mL, 80 mmol), followed by trifluoroacetic anhydride (5.6 mL, 40 mmol) dropwise. After addition, the reaction mixture was stirred at 0° C. for 5 min, then pored into H2O (50 mL), extracted with EtOAc (3×100 mL). The combined EtOAc extracts were washed with brine, dried (Na2SO4), and concentrated under reduced pressure to give a crude product, which was purified by crystallization from MeOH-EtOAc-Hexane to furnish the title compound (2.3 g) as a white solid.

Workup

  1. additionAfter addition
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined EtOAc extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a crude product, which
  7. customwas purified by crystallization from MeOH-EtOAc-Hexane

Sources & evidence

ORD record
ord-c05ecb52b26743fa92032e02d713728c
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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