3,3-Dimethyl-6-nitroindoline → 3,3-Dimethyl-2,3-dihydro-1H-indol-6-amine

HRID 1938415Notes

Reaction equation

HRID 1938415 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[NH:4][CH2:3]1>C(OCC)(=O)C.[Pd]>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:14])([CH3:1])[CH2:3][NH:4]2)=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 219594663,3-Dimethyl-6-nitroindoline

Product 1

HCID 234334683,3-Dimethyl-2,3-dihydro-1H-indol-6-amineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,3-dimethyl-6-nitroindoline (60 mg, 0.31 mmol) in 3 mL of ethyl acetate was hydrogenated under an atmosphere of hydrogen with Pd-C 10% (10 mg) at rt for 3 h. Filtration over celite afforded 45 mg (90%) of 6-amino-3,3-dimethylindoline. Data for 6-amino-3,3-dimethylindoline: 1H NMR (400 MHz, CDCl3)6.80 (d, J=7.8, 1H), 6.08 (dd, J=7.8, 2.1, 1H), 6.01 (d, J=2.1, 1H), 3.60 (bs, 1H), 3.50 (bs, 2H), 3.26 (s, 2H), 1.25 (s, 6H).

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-687f9f1918ca45669c14e0fff96bcc8c
Source dataset
uspto-grants-1997_12
Patent number
US05693646

Reaction notes

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