Hydroxylamine → HCID 18376534, compound

HRID 2300579Notes

Reaction equation

HRID 2300579 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=O)[C:11]([C:17]([CH3:21])([CH3:20])[CH:18]=[O:19])=[CH:10][C:9]2=[O:22])[CH2:2][CH2:3][CH3:4].[NH2:23][OH:24]>CO.O>[CH2:1]([O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:12]3[C:11]([C:17]([CH3:21])([CH3:20])[CH:18]([OH:19])[N+:23]=3[O-:24])=[CH:10][C:9](=[O:22])[C:8]=2[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 18376536HCID 18376536, compound2×

Product 1

HCID 18376534HCID 18376534, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2-(6-Butoxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-2-methylpropanal (compound 5 prepared in step (I) above) (53 mg, 0.18 mmol) in MeOH (5 mL) and water (0.5 mL), 50% NH2OH in water solution (17 μL, 0.28 mmol) was added. The mixture was stirred 3 h at room temp and the solvent was evaporated. The crude product was fairly pure and was taken into the next step without further purification. Yield: 52 mg (92%). 1H NMR (400 MHz, CDCl3) δ 0.99 (tr., 3H), 1.38 (s, 3H), 1.52 (s, 3 H), 1.55 (m, 2 H), 1.84 (quint., 2H), 4.13 (tr., 2H), 5.31 (s, 1 H), 6.43 (s, 1H), 7.24 (d, 1 H), 7.73 (d, 1 H), 9.07 (d, 1 H).

Workup

  1. customthe solvent was evaporated
  2. customwas taken into the next step without further purification

Sources & evidence

ORD record
ord-de2de10226d840148c6e9eaa18f99790
Source dataset
uspto-grants-2002_12
Patent number
US06498182B2

Reaction notes

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