Water → (Z)-5-amino-1,3-dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

HRID 382056Notes

Reaction equation

HRID 382056 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[C:15]4[C:11]=3/[C:12](=[CH:23]/[C:24]3[NH:25][CH:26]=[CH:27][C:28]=3[O:29][CH3:30])/[C:13](=[O:22])[NH:14]4)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O.[Cl-].[NH4+]>CO.C1COCC1.[Zn]>[NH2:19][C:18]1[C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][CH:2]=[CH:3]3)=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:22])/[C:12]/2=[CH:23]\[C:24]1[NH:25][CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 18363853(Z)-1,3-dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

Product 1

HCID 18363904(Z)-5-amino-1,3-dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)-1,3-dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (33 mg, 0.08 mmol) (from Step A above) in 1 mL of a 10% water in methanol solution and 0.5 mL THF was added zinc dust (145 mg, 2.21 mmol) followed by ammonium chloride (14 mg, 0.26 mmol). The reaction was heated at gentle reflux for 4 hours, at which time the reaction mixture was filtered through a pad of Celite® and rinsed thoroughly with ethyl acetate. The resulting solution was diluted with 5 mL water and the product was extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and concentrated. The resulting powder was recrystallized from EtOAc/hex to give (Z)-5-amino-1,3-dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one as a red powder. (Yield 24 mg, 80%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat gentle reflux for 4 hours, at which time the reaction mixture
  3. filtrationwas filtered through a pad of Celite®
  4. washrinsed thoroughly with ethyl acetate
  5. additionThe resulting solution was diluted with 5 mL water
  6. extractionthe product was extracted with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe resulting powder was recrystallized from EtOAc/hex

Sources & evidence

ORD record
ord-fd49235e4a5c45dba58b1f46ea1857b8
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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