6-chloro-4-methyl-8-nitro-9H-beta-carboline → 6-chloro-4-methyl-9H-beta-carbolin-8-ylamine

HRID 552222Notes

Reaction equation

HRID 552222 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:15]([O-])=O)[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([CH3:18])[C:5]2=1>CO.[Pt]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:15])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([CH3:18])[C:5]2=1

Participants

4

Reactant 1

HCID 671650046-chloro-4-methyl-8-nitro-9H-beta-carboline

Product 1

HCID 593375486-chloro-4-methyl-9H-beta-carbolin-8-ylamineYield 93.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-chloro-4-methyl-8-nitro-9H-β-carboline (80 mg, 0.31 mmol) in MeOH (10 ml) was stirred at RT. Platinum (10% wt. on carbon, 24 mg) catalyst was added thereto and the reaction vessel was capped and vacuum purged 3 times with argon, followed similarly by hydrogen. The reaction mixture was stirred 1.5 hr under 1 atm hydrogen, then vacuum purged with argon, diluted with DCM (10 ml) and filtered through a 0.2 μM syringe filter. The filtrate was concentrated to yield 6-chloro-4-methyl-9H-β-carbolin-8-ylamine (67 mg) as a light brown oil. 1H-NMR (300 MHz, DMSO-d6): δ 9.04 (s, 1); 8.29 (s, 1); 7.74 (d, 1); 7.10 (d, 1); 2.98 (s, 3). NH4OAc standard conditions. DAD Rf=1.89 min. M+H=231.

Workup

  1. customthe reaction vessel was capped
  2. customvacuum purged 3 times with argon
  3. customvacuum purged with argon
  4. additiondiluted with DCM (10 ml)
  5. filtrationfiltered through a 0.2 μM syringe
  6. filtrationfilter
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6a28064ebb9c402bba6ab6bf8171f0ad
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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