Hydroxylamine → 9-(4-Fluorobenzyl)-N-Hydroxy-9h-Beta-Carboline-3-Carboxamide

HRID 722118

Reaction equation

HRID 722118 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([O:16]CC)=O)[N:2]=1.[H-].[Na+].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.[NH2:30][OH:31]>CN(C=O)C.CO.O>[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:12]2[C:13]3[CH:1]=[N:2][C:3]([C:14]([NH:30][OH:31])=[O:16])=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 105078Ethyl Beta-Carboline-3-Carboxylate

Product 1

HCID 30134599-(4-Fluorobenzyl)-N-Hydroxy-9h-Beta-Carboline-3-CarboxamideYield 39%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 9H-β-carboline-3-carboxylate (368 mg, 1.53 mmol) in DMF (4 mL) under a nitrogen atmosphere was added NaH (61.2 mg, 60% in mineral oil, 1.53 mmol) portionwise, followed by 4-fluorobenzyl bromide (0.19 mL, 1.53 mmol). Stirring was continued for 24 hours at ambient temperature, water (10 mL) was then added to the mixture. The precipitate was filtered, washed with water and dried to give a solid that was dissolved in methanol (20 mL). To the resulting solution, H2NOH (20 mL, 50 wt. % solution in H2O, 0.30 mol) was added. The suspension was stirred for 5 days at ambient temperature. The mixture was then filtered, and the solid was boiled in methanol (40 mL). After filtration, the title product (0.20 g, 39%) was obtained. 1H NMR (300 MHz, DMSO-d6): δ 11.28 (1H, s), 9.02–9.08 (2H, m), 8.85 (1H, s), 8.48 (1H, d, J=9.0 Hz), 7.10–7.84 (7H, m), 5.85 (2H, s). HRMS (M+H)+ found: 336.1157. Calcd for C19H15N3O2F: 336.1148.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customto give a solid
  5. stirringThe suspension was stirred for 5 days at ambient temperature
  6. filtrationThe mixture was then filtered
  7. filtrationAfter filtration

Sources & evidence

ORD record
ord-ab202bdd67744da588d578813329d47f
Source dataset
uspto-grants-2006_11
Patent number
US07138408B2

Linked notes

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