6-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole → 6-chloro-7-fluoro-9H-beta-carbolin-8-ylamine

HRID 12197Notes

Reaction equation

HRID 12197 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:16]([O-])=O)[C:14]=1[F:15])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:16])[C:14]=1[F:15])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

4

Reactant 1

HCID 593375336-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole

Product 1

HCID 671655216-chloro-7-fluoro-9H-beta-carbolin-8-ylamineYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A slurry of 6-chloro-7-fluoro-8-nitro-9H-β-carboline (500 mg, 1.88 mmol) in MeOH (25 ml) was degassed with argon. Palladium on charcoal (20% w/w on C, 50 mg) was added and the reaction vessel was flushed with hydrogen. The slurry was stirred under a balloon of hydrogen for 6 hr, then filtered through celite and concentrated under reduced pressure to yield 6-chloro-7-fluoro-9H-β-carbolin-8-ylamine (400 mg) as a brown solid.

Workup

  1. customthe reaction vessel was flushed with hydrogen
  2. filtrationfiltered through celite and
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4fd2ab0b382a4a5fafaa30220b5f686c
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Reaction notes

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