Methanol → 6-chloro-4-fluoro-8-nitro-9H-beta-carboline

HRID 12236

Reaction equation

HRID 12236 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[Na+].[Cl:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]1[CH:14]=[N:13][CH:12]=[C:11]([F:20])[C:10]2=1.CO.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[Cl:6][C:7]1[CH:8]=[C:9]2[C:17](=[C:18]([N+:1]([O-:4])=[O:2])[CH:19]=1)[NH:16][C:15]1[CH:14]=[N:13][CH:12]=[C:11]([F:20])[C:10]2=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24268Sodium NitrateHCID 516892Sodium BicarbonateHCID 593375246-Chloro-4-fluoro-9H-beta-carboline

Product 1

HCID 671659696-chloro-4-fluoro-8-nitro-9H-beta-carbolineYield 102.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
70 °C

Procedure

Sodium nitrate (1.5 eq, 53 mmol, 4.5 g) was added portionwise to a solution of Intermediate 65 (1.0 eq, 35 mmol, 7.8 g) in trifluoroacetic acid (200 mL) and the resulting mixture heated at 70° C. for 3 h. After cooling to RT the trifluoroacetic acid was removed on a rotary evaporator to afford a crude solid which was suspended in a small volume of methanol and added dropwise to a vigorously stirred mixture of saturated sodium bicarbonate solution (500 mL). The resulting slurry was stirred for 15 min then the precipitated solids were collected by suction filtration, washed with water (300 mL) and then dried in vacuo to afford 6-chloro-4-fluoro-8-nitro-9H-β-carboline (about 9.5 g) which was used in the subsequent step without further purification.

Workup

  1. customwas removed on a rotary evaporator
  2. customto afford a crude solid which
  3. filtrationthe precipitated solids were collected by suction filtration
  4. washwashed with water (300 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-981b4dc1e0c84bf89a142b850617dd70
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Linked notes

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