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

HRID 382060Notes

Reaction equation

HRID 382060 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[C:15]3[C:11]=2/[C:12](=[CH:23]/[C:24]2[NH:25][CH:26]=[CH:27][C:28]=2[O:29][CH3:30])/[C:13](=[O:22])[NH:14]3)=[CH:6][CH:5]=1.[Cl-].[NH4+]>O.CO.[Zn]>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]([NH2:19])=[CH:17][CH:16]=[C:15]3[C:11]=2/[C:12](=[CH:23]/[C:24]2[NH:25][CH:26]=[CH:27][C:28]=2[O:29][CH3:30])/[C:13](=[O:22])[NH:14]3)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 9823378(Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester

Product 1

HCID 9821703(Z)-4-[5-amino-2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl) methylene]-2-oxo-1H-indol-4-yl]-benzoic acid methyl esterYield 51%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Using Method L above, (Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl) methylene]-5-nitro-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester (85 mg, 0.22 mmol) (from Example 45 supra) was reduced with zinc (130 mg, 1.97 mmol) and ammonium chloride (25.8 mg, 0.48 mmol) in 10% water in methanol (10 mL) at reflux for 2 h to yield (Z)-4-[5-amino-2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl) methylene]-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester (yield: 40 mg, 51%).

Workup

  1. temperatureat reflux for 2 h

Sources & evidence

ORD record
ord-8aa030c341d846429bcddc959333800a
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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