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

HRID 2109559Notes

Reaction equation

HRID 2109559 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

Alternatively, substituted amino-indolines 71 are prepared from the nitroindoline 66. Nitroindoline 66, is reacted with an acid chloride to form an amide. Further treatment with a primary or secondary amine, preferably a secondary amine, such as in the presence of NaI, at a temperature above about 50° C., and preferably at about 70° C. yields the nitroindoline 69. The nitro compound 69 is hydrogenated, such as with H2 in the presence of a catalyst, such as Pd/C, to yield the amino-indoline) 70. The carbonyl is reduced, such as with BH3-THF yields 1-aminoalkyl-indolines 71.

Sources & evidence

ORD record
ord-165c64991e3347b4941ac443fda60baf
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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