Water → HCID 10178126, compound

HRID 428699Notes

Reaction equation

HRID 428699 reaction equation
[OH:1][CH:2]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=1)[C:3]#[C:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1/[C:7](=[CH:15]/[C:16]1[NH:17][CH:18]=[CH:19][C:20]=1[O:21][CH3:22])/[C:8](=[O:14])[NH:9]2.O.[Cl-].[NH4+]>CO.[Zn]>[NH2:29][C:25]1[CH:24]=[C:23]([CH:2]([OH:1])[C:3]#[C:4][C:5]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:6]=2/[C:7](=[CH:15]/[C:16]2[NH:17][CH:18]=[CH:19][C:20]=2[O:21][CH3:22])/[C:8](=[O:14])[NH:9]3)[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 10112522HCID 10112522, compound

Product 1

HCID 10178126HCID 10178126, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

rac-(Z)-1,3-Dihydro-4-[3-hydroxy-3-(3-nitrophenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (25 mg, 0.068 mmol) (from Example 60) was added to 10% H2O in methanol (2 mL) and to this mixture was added zinc dust (35 mg, 0.53 mmol) and ammonium chloride (10 mg, 0.19 mmol). The reaction was heated at reflux for 3 h, at which time the reaction was cooled and the solid was filtered off. The solids were washed extensively with ethyl acetate, and the ethyl acetate and methanol were evaporated in vacuo. The resulting precipitate was filtered off, dried and recrystallized from ethyl acetate/hexane to give rac-(Z)-4-[3-(3-aminophenyl)-3-hydroxy-1-propynyl]-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 19 mg, 73%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 h, at which time the reaction
  3. temperaturewas cooled
  4. filtrationthe solid was filtered off
  5. washThe solids were washed extensively with ethyl acetate
  6. customthe ethyl acetate and methanol were evaporated in vacuo
  7. filtrationThe resulting precipitate was filtered off
  8. customdried
  9. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a9ecbfae0c6e4a78ba71b0dde8845934
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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