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

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Reaction Steps

Alternatively, substituted amino-indolines 62 are prepared from the nitroindoline 57. Nitroindoline 57, 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 60. The nitro compound 60 is hydrogenated, such as with H2 in the presence of a catalyst, such as Pd/C, to yield the amino-indoline 61. The carbonyl is reduced, such as with BH3-THF, to yield 1-aminoalkyl-indolines 62.

Provenance & Evidence