Hydrazine → HCID 178450903, compound

HRID 428446Notes

Reaction equation

HRID 428446 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10](/[CH:13]=[CH:14]/[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:9](OC)[C:8](=[O:24])[NH:7][C:6]=2[CH:25]=1.[NH2:26][NH2:27]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[C:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:27][NH:26][C:9]=3[C:8](=[O:24])[NH:7][C:6]=2[CH:25]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 18358906HCID 18358906, compound

Product 1

HCID 178450903HCID 178450903, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slurry of t-butyl(E)-3-(8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepin-4-yl)acrylate (prepared as described in Example 44 of WO94/29275 published Dec. 22, 1994) (0.81 g, 2.2 mmol) in methanol (5 mL) was added anhydrous hydrazine (0.14 g, 4.5 mmol) dropwise via syringe. The resulting bright yellow mixture immediately darkened to an orange color. After 45 minutes of stirring at room temperature, the reaction mixture became a thick yellow-orange slurry which was allowed to stir for an additional 18 hours. The reaction mixture was filtered to give a solid which was recrystallized from ethanol. Very little product was recovered and the filtrate was concentrated and purified with a silica gel plug using ethyl acetate:hexanes (50:50) as the eluent to give an orange oil. This was allowed to crystallize in ethanol at −10° C. for 18 hours, filtered and dried at 100° C. to give the title compound (0.2 g, 25%, m.p. 226.5-228.6° C.).

Workup

  1. stirringto stir for an additional 18 hours
  2. filtrationThe reaction mixture was filtered
  3. customto give a solid which
  4. customwas recrystallized from ethanol
  5. customVery little product was recovered
  6. concentrationthe filtrate was concentrated
  7. custompurified with a silica gel plug
  8. customto give an orange oil
  9. customto crystallize in ethanol at −10° C. for 18 hours
  10. filtrationfiltered
  11. customdried at 100° C.

Sources & evidence

ORD record
ord-5a92966d8b0144ae85f50bd12e9791b1
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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