Hydrochloric Acid → 4-(3-Formyl-6-nitroindol-1-yl)benzoic acid ethyl ester

HRID 1674608Notes

Reaction equation

HRID 1674608 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[CH:13]=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].Cl.CN(C)[CH:34]=[O:35]>>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[C:13]([CH:34]=[O:35])=[CH:12]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 584372194-(6-Nitroindol-1-yl)benzoic acid ethyl ester

Product 1

HCID 866396014-(3-Formyl-6-nitroindol-1-yl)benzoic acid ethyl ester

Conditions

Temperature
70 °C

Procedure

To a solution of 4-(6-nitroindol-1-yl)benzoic acid ethyl ester (0.53 g) in N,N-dimethylformamide (6 mL) was added phosphoryl chloride (0.31 g) under ice cooling and this mixture was stirred at 70° C. overnight. After cooling to ambient temperature, to this reaction mixture was added 2 mol/L aqueous sodium hydroxide solution and this mixture was stirred at 30 minutes. This reaction mixture was poured into 1 mol/L hydrochloric acid, and the precipitated solid was collected by filtration, and washed with water and n-hexane, and dried under reduced pressure at 40° C. to give 4-(3-formyl-6-nitroindol-1-yl)benzoic acid ethyl ester (0.46 g). To a solution of this aldehyde (0.46 g) in tetrahydrofuran (10 mL) were added hydroxylamine hydrochloride (0.19 g) and pyridine (0.43 g) at room temperature, and this mixture was stirred at 80° C. for 8 hours. To this reaction mixture was added acetic anhydride (0.42 g) at 80° C., this mixture was stirred at same temperature overnight. After cooling to ambient temperature, to this reaction mixture was added 1 mol/L hydrochloric acid, and the precipitated solid was collected by filtration. This solid was washed with water, n-hexane and diethyl ether to give the title compound (0.13 g).

Workup

  1. temperatureAfter cooling to ambient temperature, to this reaction mixture
  2. stirringthis mixture was stirred at 30 minutes
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water and n-hexane
  5. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-9186ad31586143c7b628c99a21dea6d7
Source dataset
uspto-grants-2011_08
Patent number
US08003647B2

Reaction notes

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