Water → HCID 66961449, compound

HRID 69064Notes

Reaction equation

HRID 69064 reaction equation
[O:1]=[C:2]1[C:10](=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:33]=[CH:32][C:19]2[N:20]([CH2:30][CH3:31])[C:21](=[O:29])[C:22]([CH3:28])([CH3:27])[C:23](=[O:26])[N:24]([CH3:25])[C:18]=2[CH:17]=1.O>O.NN>[CH2:30]([N:20]1[C:21](=[O:29])[C:22]([CH3:28])([CH3:27])[C:23](=[O:26])[N:24]([CH3:25])[C:18]2[CH:17]=[C:16]([O:15][CH2:14][CH2:13][CH2:12][N:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:10][C:2]3=[O:1])[CH:33]=[CH:32][C:19]1=2)[CH3:31]

Participants

4

Reactant 2

HCID 962WaterHCID 66961177HCID 66961177, compound

Product 1

HCID 66961449HCID 66961449, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

7-[3-(2,3-Dioxo-2,3-dihydroindol-1-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.3 g) was suspended in hydrazine hydrate (3 ml), and the liquid was stirred for two hours while heated under reflux. The reaction mixture was cooled to room temperature. Water was added thereto, followed by extraction by ethyl acetate. The organic layer was dried by anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=85:15). The purified product was condensed under reduced pressure, and the residue was recrystallized from ether/hexane, thereby obtaining the title compound (0.18 g) as a pale brownish white powder.

Workup

  1. temperaturewhile heated
  2. temperatureunder reflux
  3. extractionfollowed by extraction by ethyl acetate
  4. dry with materialThe organic layer was dried by anhydrous sodium sulfate, and condensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=85:15)
  6. customcondensed under reduced pressure
  7. customthe residue was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-ac7601b9049e41ac8c10308a8a2b2789
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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