Hydroxylamine → HCID 3013462, compound

HRID 722121Notes

Reaction equation

HRID 722121 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+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[NH2:29][OH:30]>CN(C=O)C.CO.O>[CH2:21]([N:12]1[C:13]2[CH:1]=[N:2][C:3]([C:14]([NH:29][OH:30])=[O:16])=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 105078Ethyl Beta-Carboline-3-Carboxylate

Product 1

HCID 3013462HCID 3013462, compoundYield 39.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 9H-β-carboline-3-carboxylate (290 mg, 1.21 mmol) in DMF (4 mL) under a nitrogen atmosphere was added NaH (53 mg, 60% in mineral oil, 1.33 mmol) portionwise, followed by benzyl bromide (173 μL, 1.45 mmol). Stirring was continued for 21 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 (25 mL). To the resulting solution, H2NOH (25 mL, 50 wt. % solution in H2O, 0.38 mol) was added. The suspension was stirred for 3 days at ambient temperature. The mixture was then filtered, and the solid was boiled in methanol (25 mL). After filtration, the title product (0.15 g, 39%) was obtained. 1H NMR (400 MHz, DMSO-d6): δ 11.32 (1H, s), 9.10 (1H, s), 9.05 (1H, s), 8.89 (1H, s), 8.52 (1H, d, J=8 Hz), 7.26–7.87 (8H, m), 5.90 (2H, s). HRMS (M+H)+ found: 318.1249. Calcd for C19H16N3O2: 318.1243.

Workup

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

Sources & evidence

ORD record
ord-ba013fc8297c4df5a4441018853493b3
Source dataset
uspto-grants-2006_11
Patent number
US07138408B2

Reaction notes

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