Water → HCID 68999229, compound

HRID 1821388Notes

Reaction equation

HRID 1821388 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[N+:27]([O-])=O)[C:19]2=[O:30])=[N:2]1.[Cl-].[NH4+].O>C(OCC)(=O)C.CCCCCC.[Fe]>[NH2:27][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:25]=1[CH2:26][N:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1/[CH:11]=[CH:10]/[C:3]1[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=1)[C:19]2=[O:30]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 69002133HCID 69002133, compound

Product 1

HCID 68999229HCID 68999229, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of (E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}-4-nitro-2,3-dihydroisoindol-1-one (54 mg, 0.14 mmol) obtained in Step 1 in ethanol/water (2/1, 3.3 mL), ammonium chloride (40 mg, 0.75 mmol) and iron (38 mg, 0.68 mmol) were added, followed by heating under reflux for 4.0 hours under nitrogen atomosphere. The reaction mixture was added with water, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10) and crystallized from hexane/ethyl acetate (1/1) to obtain Compound 216 (10 mg, 20%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4.0 hours under nitrogen atomosphere
  3. extractionextracted with ethyl acetate
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10)
  6. customcrystallized from hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-dc2526e15da14bbd9046f3f62904b214
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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