Hydrochloric Acid → HCID 25051857, compound

HRID 73364Notes

Reaction equation

HRID 73364 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[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)[C:13]([CH:23]=O)=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].Cl.[NH2:27]O.C(OC(=O)C)(=O)C.Cl>O1CCCC1.N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:25])[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)[C:13]([C:23]#[N:27])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 866396014-(3-Formyl-6-nitroindol-1-yl)benzoic acid ethyl ester

Product 1

HCID 25051857HCID 25051857, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °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. stirringthis mixture was stirred at same temperature overnight
  2. temperatureAfter cooling to ambient temperature, to this reaction mixture
  3. filtrationthe precipitated solid was collected by filtration
  4. washThis solid was washed with water, n-hexane and diethyl ether

Sources & evidence

ORD record
ord-40a5fc46940b4db399b1a4975d2b752e
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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