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

HRID 382052Notes

Reaction equation

HRID 382052 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[C:13]3[C:9]=2/[C:10](=[CH:21]/[C:22]2[NH:23][CH:24]=[CH:25][C:26]=2[O:27][CH3:28])/[C:11](=[O:20])[NH:12]3)=[CH:4][CH:3]=1.[Cl-].[NH4+]>O.CO.[Zn]>[NH2:17][C:16]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:20])/[C:10]/2=[CH:21]\[C:22]1[NH:23][CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 9951621(Z)-1,3-dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

Product 1

HCID 9798339(Z)-5-amino-1,3-dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-oneYield 49.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Using Method L above, (Z)-1,3-dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (84 mg, 0.22 mmol) (from Example 37 supra) was reduced with zinc (130 mg, 2.0 mmol) and ammonium chloride (25.9 mg, 0.48 mmol) in 10% water in methanol (20 mL) at reflux for 18 h to give (Z)-5-amino-1,3-dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (yield: 38 mg, 49%).

Workup

  1. temperatureat reflux for 18 h

Sources & evidence

ORD record
ord-edf0d29d4ead42e8899ed8465a0f432f
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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