Hydroxylamine → HCID 11522747, compound

HRID 501179Notes

Reaction equation

HRID 501179 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([O-:21])=O)=[CH:17][N:16]=1)[CH2:7][CH2:6]2.[NH2:24][OH:25].[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:24][OH:25])=[O:21])=[CH:17][N:16]=1)[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 86607541HCID 86607541, compound

Product 1

HCID 11522747HCID 11522747, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)nicotinate (12 mg) in dioxane (0.8 mL) was treated with 50% aqueous hydroxylamine (0.2 mL). After 10 minutes the reaction was treated with 1N sodium hydroxide (0.06 mL) and the solution stirred for 72 hours. The reaction was quenched with 1N hydrochloric acid (0.06 mL) and the solvent was evaporated. The residue was purified by preparative hplc and the pure samples freeze dried to give 6-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-N-hydroxynicotinamide as a yellow solid (7.9 mg), m/e=330 (M+1). 1H NMR (DMSOd6) ppm: 2.8 (2H, m), 3.72 (6H, s) 3.9 (2H, m), 4.7 (2H, s), 6.76 (1H, s), 6.83 (1H, s), 6.9 (1H, d), 7.9 (1H, m), 8.55 (1H, s), 11 (1H, bs).

Workup

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

Sources & evidence

ORD record
ord-9cbe4d41e0df4f338be4bfeb5520ed81
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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