Ethyl Acetate → 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(3-pyridinyl)-2E-propenyl]hydrazide

HRID 1768765Notes

Reaction equation

HRID 1768765 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C:7]3[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=3[CH2:9][N:10]([C:11]([NH:13][NH2:14])=[O:12])[C:4]=2[CH:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=[CH:28][C:29](O)=[O:30])[CH:22]=1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C)C=O>[O:30]=[C:29]([NH:14][NH:13][C:11]([N:10]1[CH2:9][C:8]2[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=2[O:6][C:5]2[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][C:4]1=2)=[O:12])/[CH:28]=[CH:27]/[C:23]1[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1019843-(3-Pyridinyl)-2-propenoic acidHCID 135604618-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, hydrazide

Product 1

HCID 149759868-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(3-pyridinyl)-2E-propenyl]hydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2.82 g (9.7 mmol) of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, hydrazide (1), prepared as described above in Example 1, in 25 mL of dimethyl formamide (DMF) cooled in an ice bath was added 1.54 g (9.7 mmol) of 3-(3-pyridyl)acrylic acid. To the heterogenous mixture was added 1.74 mL (10 mmol) of N,N-diisopropylethylamine and 1.92 g (10 mmol) of N,N-dimethylaminopropylethylcarbodiimide hydrochloride. The reaction was stirred over night at ambient temperature. To the reaction was added 100 mL of ethyl acetate (EtOAc) and 100 mL of a saturated solution of KHCO3. The resulting layers were separated, and the organic layer was washed three times with saturated KHCO3 and two times with water. The organic layer was then dried over Na2SO4 anhydrous and filtered. The solvent was removed under vacuum, and the resultant solid was chromatographed. The yield of isolated product was 2.16 g (53%). Analysis calculated for C22H17N4O3Cl (M.W. 420.86): C, 62.79; H, 4.07; N, 13.31; Cl, 8.42. Found: C, 62.72; H, 4.27; N, 12.78; Cl 8.21.

Workup

  1. temperaturecooled in an ice bath
  2. customThe resulting layers were separated
  3. washthe organic layer was washed three times with saturated KHCO3 and two times with water
  4. dry with materialThe organic layer was then dried over Na2SO4 anhydrous
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum
  7. customthe resultant solid was chromatographed

Sources & evidence

ORD record
ord-dfedab59a83a457e8459db24c56a380c
Source dataset
uspto-grants-1995_01
Patent number
US05378840

Reaction notes

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