Hydroxylamine → HCID 3013461, compound

HRID 722120Notes

Reaction equation

HRID 722120 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+].[Cl:21][C:22]1[C:23]([F:30])=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br.[NH2:31][OH:32]>CN(C=O)C.CO.O>[Cl:21][C:22]1[C:23]([F:30])=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][N:12]1[C:13]2[CH:1]=[N:2][C:3]([C:14]([NH:31][OH:32])=[O:16])=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 24758Sodium hydrideHCID 105078Ethyl Beta-Carboline-3-CarboxylateHCID 5228271-(Bromomethyl)-3-chloro-2-fluorobenzene

Product 1

HCID 3013461HCID 3013461, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 9H-β-carboline-3-carboxylate (400 mg, 1.66 mmol) in DMF (5 mL) under nitrogen atmosphere was added NaH (66.4 mg, 60% in mineral oil, 1.66 mmol) portionwise, followed by 3-chloro-2-fluoro-benzyl bromide (371 mg, 1.66 mmol). Stirring was continued for 25 hours at ambient temperature, water (30 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 (25 mL). To the resulting solution, H2NOH (25 mL, 50 wt. % solution in H2O, 0.38 mol) was added. The suspension was stirred for 4 days at ambient temperature. The mixture was then filtered, and the solid was boiled in methanol (20 mL). After filtration, the title product (0.19 g, 31%) was obtained. 1H NMR (400 MHz, DMSO-d6): δ 11.33 (1H, s), 9.08 (1H, s), 9.04 (1H, s), 8.89 (1H, s), 8.51 (1H, d, J=8 Hz), 6.95–7.81 (6H, m), 6.00 (2H, s). HRMS (M+H)+ found: 370.0764. Calcd for C19H14N3O2FCl: 370.0759.

Workup

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

Sources & evidence

ORD record
ord-ccec4b5e2b4f4bbfaf09f13b12e508d2
Source dataset
uspto-grants-2006_11
Patent number
US07138408B2

Reaction notes

Loading…