Water → HCID 9923334, compound

HRID 428724Notes

Reaction equation

HRID 428724 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:21])/[C:15]/3=[CH:22]\[C:23]2[NH:24][CH:25]=[CH:26][CH:27]=2)=[CH:6][CH:5]=1)([O-])=O.O.[Cl-].[NH4+]>CO.C1COCC1.[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:21])/[C:15]/3=[CH:22]\[C:23]2[NH:24][CH:25]=[CH:26][CH:27]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 9968539HCID 9968539, compound

Product 1

HCID 9923334HCID 9923334, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)-1,3-dihydro-5-(4-nitrophenyl)ethynyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (45 mg, 0.13 mmol) (from Example 89) in 1 mL of a 10% water in methanol solution and 0.5 mL THF was added zinc dust (145 mg, 2.21 0 mmol) followed by ammonium chloride (25 mg, 0.47 mmol). The reaction was heated at gentle reflux for 4 hours, at which time the reaction mixture was filtered through a pad of Celite® (Fisher Scientific) 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-(4-aminophenyl)ethynyl-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one as a red powder. (Yield 24 mg, 56%).

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® (Fisher Scientific)
  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-758a1e9217414635a36cfb4780baf9e6
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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