Hydrochloric Acid → 2-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine

HRID 1851395Notes

Reaction equation

[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[N+:15]([O-])=O.[Cl-].[Ca+2].[Cl-].C(O)C.Cl>[Fe].O>[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:15]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-(4,5-dihydro-1,3-thiazol-2-yl)-7-nitro-1H-indole (4.0 g), iron powder (4.0 g), calcium chloride (770 mg), ethanol (45 mL) and water (5 mL) was added 1N hydrochloric acid (0.2 mL), and the mixture was stirred at 80° C. for 2 hr. After cooling the reaction mixture to room temperature, and the insoluble material was filtered off. Saturated aqueous sodium hydrogen carbonate was added to the filtrate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate) to give the title compound (1.9 g, yield 56%) as pale-yellow crystals.

Workup

temperatureAfter cooling the reaction mixture to room temperature
filtrationthe insoluble material was filtered off
additionSaturated aqueous sodium hydrogen carbonate was added to the filtrate
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-1b5a6b348f2d433c85f04fcbca758cf7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957070B2

Reaction notes

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