Hydroxylamine → HCID 58703298, compound

HRID 501177Notes

Reaction equation

HRID 501177 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:14]1[CH:22]=[CH:21][C:17]([C:18]([O-:20])=O)=[CH:16][N:15]=1.[NH2:23][OH:24].[OH-].[Na+]>O1CCOCC1>[OH:24][NH:23][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][C:14]([N:2]2[CH2:3][CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 86607540HCID 86607540, compound

Product 1

HCID 58703298HCID 58703298, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-(1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)nicotinate (12 mg) in dioxane (1.5 mL) was treated with 50% aqueous hydroxylamine (0.2 mL). After 15 minutes, 1N sodium hydroxide (0.06 mL) was added and the reaction was stirred for 72 hours. The reaction was quenched with 1N hydrochloric acid (0.06 mL) and the solvent evaporated. The residue was purified by preparative hplc and the pure samples freeze dried to give N-hydroxy-6-(1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)nicotinamide as a yellow solid (4 mg), m/e=308 (M+1). 1H NMR (DMSOd6) ppm: 2.8 (2H, m), 4.05 (2H, m), 4.85 (2H, s), 6.9-7.08 (3H, m), 7.29 (1H, d), 7.39 (1H, d), 7.87-7.91 (1H, m), 8.5 (1H m), 10.9 (1H, s), 11.05 (1H, bs).

Workup

  1. customThe reaction was quenched with 1N hydrochloric acid (0.06 mL)
  2. customthe solvent evaporated
  3. customThe residue was purified by preparative hplc
  4. customthe pure samples freeze dried

Sources & evidence

ORD record
ord-7e2bd0860018434c840e66375761989c
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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