Sodium Bicarbonate → 6-Chloro-7-methoxy-9h-pyrido[3,4-b]indol-8-amine

HRID 12179

Reaction equation

HRID 12179 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:17]([O-])=O)[C:14]=1[O:15][CH3:16])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[H][H].C([O-])(O)=O.[Na+]>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:17])[C:14]=1[O:15][CH3:16])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 593375346-chloro-7-methoxy-8-nitro-9H-pyrido[3,4-b]indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 213627436-Chloro-7-methoxy-9h-pyrido[3,4-b]indol-8-amineYield 112.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

6-chloro-7-methoxy-8-nitro-9H-β-carboline (510 mg, 1.84 mmol) was suspended in 50 ml of methanol and 100 mg of Pd/C (10%) was added. The flask was fitted with a balloon of hydrogen and the reaction mixture was stirred overnight at RT. Upon filtration through a pad of celite and evaporation of the methanol, a dark brown solid was obtained. This residue was suspended in methanol (15 ml) and added, with vigorous stirring, to a solution of saturated NaHCO3 (100 ml). The light brown solid that precipitated out was collected by filtration and dried thoroughly in vacuo to give the desired product (512 mg, quantitative yield).

Workup

  1. filtrationUpon filtration
  2. customthrough a pad of celite and evaporation of the methanol
  3. customa dark brown solid was obtained
  4. customThe light brown solid that precipitated out
  5. filtrationwas collected by filtration
  6. customdried thoroughly in vacuo

Sources & evidence

ORD record
ord-becf4864ac49431f98c4bd814a232da9
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Linked notes

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