6-Nitroindoline → Indolin-6-amine

HRID 1604804Notes

Reaction equation

HRID 1604804 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 297576-Nitroindoline

Product 1

HCID 34185Indolin-6-amineYield 122.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-nitroindoline (1 g, 6.1 mmol) in 50 mL of ethyl acetate was hydrogenated under an atmosphere of hydrogen with Pd-C 10% (100 mg) at rt for 3 h. Filtration over celite afforded 1.0 g (98%) of 6-aminoindoline. Data for 6-aminoindoline: 1H NMR (400 MHz, CDCl3) 7.40 (d, J=7.4, 1H), 6.05 (d, J=2.0, 1H), 6.03 (d, J=7.5, 1H), 3.67 (bs, 1H), 3.49 (t, J=8.1, 2H), 3.48 (bs, 2H), 2.90 (t, J=8.2, 2H).

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-99fc4e9bb2324755a7819f5f2d5b076f
Source dataset
uspto-grants-1999_11
Patent number
US05994544

Reaction notes

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