Sodium Acetate → 3-Acetyl-8-(3-fluoro-benzyloxy)-1,3-dihydro-benzo[d]azepin-2-one

HRID 346456Notes

Reaction equation

HRID 346456 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[CH2:12][C:11]=2[CH:18]=1.[C:22]([O-])(=[O:24])[CH3:23].[Na+]>C(OC(=O)C)(=O)C>[C:22]([N:14]1[CH:15]=[CH:16][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]3[CH:19]=[CH:20][CH:21]=[C:2]([F:1])[CH:3]=3)=[CH:18][C:11]=2[CH2:12][C:13]1=[O:17])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 112545798-(3-Fluoro-benzyloxy)-1,3-dihydro-benzo[d]azepin-2-one

Product 1

HCID 114501873-Acetyl-8-(3-fluoro-benzyloxy)-1,3-dihydro-benzo[d]azepin-2-oneYield 77.7%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
140 °C

Procedure

In a dried flask under an inert atmosphere, 103 mg (0.36 mmol) of 8-(3-fluoro-benzyloxy)-1,3-dihydro-benzo[d]azepin-2-one and 72 mg (0.9 mmol) of sodium acetate were suspended in 0.3 ml of acetic acid anhydride. The solution was heated to 140° C. for 4 h. For the working-up, the reaction mixture was cooled, then evaporated under reduced pressure. The residue was treated with 1.5 ml of ice/water and 4 ml of ethyl acetate. The aqueous layer was separated and re-extracted with 4 ml of ethyl acetate. The combined organic layers were dried over sodium sulfate, thereafter the solvent evaporated under reduced pressure. For purification, the crude material obtained was chromatographed on silica gel using a gradient of heptane to a 4:1-mixture of heptane and ethyl acetate as the eluent. There were obtained 91 mg (77% of theory) of 3-acetyl-8-(3-fluoro-benzyloxy)-1,3-dihydro-benzo[d]azepin-2-one as a light yellow solid; MS: m/e=325 (M)+.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customevaporated under reduced pressure
  3. additionThe residue was treated with 1.5 ml of ice/water and 4 ml of ethyl acetate
  4. customThe aqueous layer was separated
  5. extractionre-extracted with 4 ml of ethyl acetate
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. customthe solvent evaporated under reduced pressure
  8. customFor purification
  9. customthe crude material obtained
  10. customwas chromatographed on silica gel using a gradient of heptane to a 4

Sources & evidence

ORD record
ord-f767cf8bff294e0e9616cc43734f2974
Source dataset
uspto-grants-2007_02
Patent number
US07173023B2

Reaction notes

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