Nitroindoline → 2,3-dihydro-1H-indol-1-amine

HRID 2109558Notes

Reaction equation

HRID 2109558 reaction equation
[N+:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)([O-])=O>[Pd]>[NH2:1][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

3

Reactant 1

HCID 21959507Nitroindoline

Product 1

HCID 27609322,3-dihydro-1H-indol-1-amine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Substituted indolines are prepared such as by the procedures described in Scheme 18. Substituted amino-indolines 68 are prepared from the nitroindoline 66 and a ketone in the presence of NaHB(OAc)3 to form the 1-substituted indoline 67. The nitroindoline 67 is hydrogenated, such as with H2 in the presence of a catalyst, such as Pd/C, to yield the amino-indoline 68.

Sources & evidence

ORD record
ord-97573edf4dd0438bae8d8cb4b4f88d75
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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