Formic Acid → 6-chloro-7-ethoxy-9H-beta-carbolin-8-ylamine

HRID 552179Notes

Reaction equation

HRID 552179 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:18]([O-])=O)[C:14]=1[O:15][CH2:16][CH3:17])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[H][H].ClC1C=C2C(=C(N)C=1OCC1CC1)NC1C=NC=CC2=1.C(O)=O>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:18])[C:14]=1[O:15][CH2:16][CH3:17])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 671651336-chloro-7-ethoxy-8-nitro-9H-beta-carbolineHCID 671652126-chloro-7-cyclopropylmethoxy-9H-beta-carbolin-8-ylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 671644526-chloro-7-ethoxy-9H-beta-carbolin-8-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-chloro-7-ethoxy-8-nitro-9H-β-carboline (160 mg, 0.55 mmol) was suspended in 4 ml of methanol and 25 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 and determined to be the desired 6-chloro-7-cyclopropylmethoxy-9H-β-carbolin-8-ylamine (80 mg, 55%). 1H-NMR (300 MHz, Methanol-d4/CDCl3): δ 1.26 (t, 3H), 3.91 (q, 2H), 7.34 (s, 1H), 7.71 (d, 1H), 8.02 (s, 1H), 8.56 (s, 1H). Retention Time (LC, method: formic acid standard): 1.16 min. MS (M+H+): 262.0.

Workup

  1. filtrationUpon filtration
  2. customthrough a pad of celite and evaporation of the methanol
  3. customa dark brown solid was obtained
  4. custom1.16 min

Sources & evidence

ORD record
ord-f8f9047e04e841ecac45b2c693c05610
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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