Sodium Bicarbonate → 6-chloro-7-cyclopropylmethoxy-9H-beta-carbolin-8-ylamine

HRID 552192Notes

Reaction equation

HRID 552192 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:20]([O-])=O)[C:14]=1[O:15][CH2:16][CH:17]1[CH2:19][CH2:18]1)[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]([NH2:20])[C:14]=1[O:15][CH2:16][CH:17]1[CH2:19][CH2:18]1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 671651746-chloro-7-cyclopropylmethoxy-8-nitro-9H-beta-carbolineHCID 178418361HCID 178418361, compound

Product 1

HCID 671652126-chloro-7-cyclopropylmethoxy-9H-beta-carbolin-8-ylamineYield 80.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

6-chloro-7-cyclopropylmethoxy-8-nitro-9H-β-carboline (510 mg, 1.61 mmol) was suspended in 12 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 (10 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 6-chloro-7-cyclopropylmethoxy-9H-β-carbolin-8-ylamine (371 mgs, 80% yield). 1H-NMR (300 MHz, methanol-d4): δ 0.36 (m, 2H), 0.61 (m, 2H), 1.37 (m, 1H), 3.88 (d, 2H), 7.58 (s, 1H), 7.96(d, 1H), 8.23 (d, 1H), 8.76 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 2.28 min. MS (M+H+): 288.

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-492f10139178472d8d70f47db3439a48
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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