Ethanol → 2-Amino-4-(3-cyanoindol-1-yl)benzoic acid

HRID 1674619Notes

Reaction equation

HRID 1674619 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([N+:21]([O-])=O)[CH:13]=2)[CH:4]=1)#[N:2].C(O)C.O.[Cl-].[NH4+]>[Zn].C(OCC)(=O)C.O1CCCC1>[NH2:21][C:14]1[CH:13]=[C:12]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]([C:1]#[N:2])=[CH:4]2)[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 58437261HCID 58437261, compound

Product 1

HCID 584372312-Amino-4-(3-cyanoindol-1-yl)benzoic acidYield 27.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(3-cyanoindol-1-yl)-2-nitrobenzoic acid (0.012 g) in a mixed solvent of ethanol (1 mL), water (0.5 mL) and tetrahydrofuran (0.5 mL) were added zinc powder (0.041 g) and ammonium chloride (0.004 g) at room temperature, and this mixture was stirred at 80° C. for 2.5 hours. After cooling to ambient temperature, to this reaction mixture was added ethyl acetate. This insoluble material was removed by filtration and this filtrate was washed with brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (0.003 g).

Workup

  1. temperatureAfter cooling to ambient temperature, to this reaction mixture
  2. customThis insoluble material was removed by filtration
  3. washthis filtrate was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-af555f64c91f4df29e5eb4b49c5f9e2c
Source dataset
uspto-grants-2011_08
Patent number
US08003647B2

Reaction notes

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