Hydrochloric Acid → 5-(3-Methyl-butanoyl)-1,3-dihydro-indol-2-one

HRID 1387402Notes

Reaction equation

[Cl-].[Cl-].[Cl-].[Al+3].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14].[CH3:15][CH:16]([CH3:21])[CH2:17][C:18](Cl)=[O:19].Cl>CN(C)C=O>[CH3:15][CH:16]([CH3:21])[CH2:17][C:18]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[NH:5][C:6](=[O:14])[CH2:7]2)=[O:19]

Participants

Conditions

Temperature: 70 °C

Procedure

Aluminum trichloride (10.7 g, 7.5 mmole) was placed in a round bottom flask under nitrogen at room temperature. Dimethylformamide (1.7 mL) was added dropwise, which produced an exothermic reaction. The reaction stood for 15 minutes before the addition of oxindole (1 g, 7.5 mmole) followed by 3-methyl-butanoyl chloride (0.96 g, 8 mmole). The reaction was heated to 70° C. for 60 minutes. The reaction was poured onto crushed ice (100 g) with concentrated hydrochloric acid added (10 mL). The aqueous layer was extracted with EtOAc (100 mL). The organic layer was washed with a saturated NaCl (aqueous) solution, dried over MgSO4. The volatiles were removed in vacuo to afford the desired compound (1.38 g, 85%). 1H NMR (DMSO-d6): d 10.71 (s, 1H); 7.82 (d, J=8, 1H); 7.77 (s, 1H); 6.86 (d, J=8, 1H); 3.51 (s, 2H); 2.76 (d, J=7, 2H); 2.13-2.05 (m, 1H ); 0.88 (d, J=7, 6H) ESI-MS: m/z 216 (m−H)−.

Workup

customwhich produced
customan exothermic reaction
additionThe reaction was poured
additionadded (10 mL)
extractionThe aqueous layer was extracted with EtOAc (100 mL)
washThe organic layer was washed with a saturated NaCl (aqueous) solution
dry with materialdried over MgSO4
customThe volatiles were removed in vacuo

Sources & evidence

ORD record: ord-81d9e734ddfa4d8bac29f0bf09c734eb
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268391B1

Reaction notes

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