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

HRID 128647Notes

Reaction equation

HRID 128647 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][1,41oxazepine-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-238f48d9a3ee47299adbca268a23b372
Source dataset
uspto-grants-1995_11
Patent number
US05464830

Reaction notes

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