Hydroxylamine → HCID 3013463, compound

HRID 722122Notes

Reaction equation

HRID 722122 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+].[CH3:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.[OH-:30].[Na+].[NH2:32]O>CN(C=O)C.CO.O>[CH3:21][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:32][OH:30])=[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

9

Reactant 5

HCID 787HydroxylamineHCID 7721p-Xylyl bromideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 105078Ethyl Beta-Carboline-3-Carboxylate

Product 1

HCID 3013463HCID 3013463, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 9H-β-carboline-3-carboxylate (400 mg, 1.67 mmol) in DMF (5 mL) under a nitrogen atmosphere was added NaH (73 mg, 60% in mineral oil, 1.76 mmol) portionwise, followed by 4-methylbenzyl bromide (308 mg, 1.67 mmol). Stirring was continued for 48 hours at ambient temperature, water (50 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 (35 mL). To the resulting solution, NaOH (2N, 1 mL) and H2NOH (35 mL, 50 wt. % solution in H2O, 0.53 mol) were added. The suspension was stirred for 7 days at ambient temperature. The mixture was then filtered and dried to the title product (0.20 g, 36%). 1H NMR (400 MHz, DMSO-d6): δ 11.25 (1H, s), 8.95–9.03 (2H, m), 8.83 (1H, s), 8.45 (1H, d, J=8 Hz), 7.05–7.81 (7H, m), 5.78 (2H, s), 2.21 (3H, s). HRMS (M+H)+ found: 332.1400. Calcd for C20H18N3O2: 332.1399.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customto give a solid
  5. stirringThe suspension was stirred for 7 days at ambient temperature
  6. filtrationThe mixture was then filtered
  7. dry with materialdried to the title product (0.20 g, 36%)

Sources & evidence

ORD record
ord-bcc0848656494fbd83104f67d7069ad4
Source dataset
uspto-grants-2006_11
Patent number
US07138408B2

Reaction notes

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