Ammonium Chloride → (Z)-5-[5-amino-2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-4-yl]-4-pentynoic acid methyl ester

HRID 366671Notes

Reaction equation

HRID 366671 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH2:5][C:6]#[C:7][C:8]1[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[C:13]2[C:9]=1/[C:10](=[CH:21]/[C:22]1[NH:23][CH:24]=[CH:25][C:26]=1[O:27][CH3:28])/[C:11](=[O:20])[NH:12]2.[Cl-].[NH4+]>O.CO.[Zn]>[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH2:5][C:6]#[C:7][C:8]1[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]2[C:9]=1/[C:10](=[CH:21]/[C:22]1[NH:23][CH:24]=[CH:25][C:26]=1[O:27][CH3:28])/[C:11](=[O:20])[NH:12]2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 20667779(Z)-5-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2-oxo-1H-indol-4-yl]-4-pentynoic acid methyl ester

Product 1

HCID 20667780(Z)-5-[5-amino-2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-4-yl]-4-pentynoic acid methyl esterYield 48%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Using Method L above, (Z)-5-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2-oxo-1H-indol-4-yl]-4-pentynoic acid methyl ester (0.22 g, 0.57 mmol) (from Example 35 above) was reduced with zinc (0.33 g, 5.1 mmol) and ammonium chloride (67.1 mg, 1.25 mmol) in 10% water in methanol (20 mL) with heating at reflux for 4 h to give (Z)-5-[5-amino-2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-4-yl]-4-pentynoic acid methyl ester (Yield 0.1 g, 48%).

Workup

  1. temperaturewith heating
  2. temperatureat reflux for 4 h

Sources & evidence

ORD record
ord-9d7fe95304284d00ab3171d2a80d5442
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

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