Water → 3,3-Dimethyl-6-nitroindoline

HRID 1939458Notes

Reaction equation

Br[C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:3]=1[NH:4][CH2:5][C:6]([CH3:8])=[CH2:7].C(N(CC)CC)C.C([O-])=O.[Na+].O>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:7][C:6]1([CH3:8])[C:2]2[C:3](=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)[NH:4][CH2:5]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-bromo-N-(2-methyl-2-propenyl)-5-nitroaniline (100 mg, 0.369 mmol), Pd(OAc)2 (2 mg, 0.0073 mol), Bu4NBr (119 mg, 0.369 mmol) and triethylamine (129 mL, 0.922 mmol) in 1 mL of dry DMF under argon atmospere was heated at 80° C. for 1 h. Then sodium formate (25 mg, 0.369 mmol) was added to the reaction mixture with continued heating at 80° C. for 20 h. Water (2 mL) was added and the mixture was extracted with ethyl acetate (2×5 mL), dried (Na2SO4) and concentrated in vacuo to an oil that was subjected to flash column chromatography (silica gel, hexanes/ethyl acetate, 8:2) to give 60 mg (80%) of 3,3-dimethyl-6-nitroindoline. Data for 3,3-dimethyl-6-nitroindoline: 1H NMR (400 MHz, CDCl3) 7.60 (dd, J=8.2, 2.0, 1H), 7.35 (d, J=2.0, 1H), 7.08 (d, J=8.2, 1H), 3.98 (bs, 1H), 3.41 (s, 2H), 1.33 (s, 6H).

Workup

extractionthe mixture was extracted with ethyl acetate (2×5 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo to an oil that

Sources & evidence

ORD record: ord-c97cbd41138f4e5d866ae76c6d01f293
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696127

Reaction notes

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