Water → 1-Amino-6-tert-butoxy4-nitronaphthalene

HRID 2306235Notes

Reaction equation

HRID 2306235 reaction equation
[C:1]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[C:13]2[N+:16]([O-:18])=[O:17])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:20]O.[OH-].[K+].O>CCO.CO>[NH2:20][C:10]1[C:9]2[C:14](=[CH:15][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:7][CH:8]=2)[C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 184336007-Tert-butoxy-1-nitronaphthalene

Product 1

HCID 184335291-Amino-6-tert-butoxy4-nitronaphthalene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 7-tert-butoxy-1-nitronaphthalene, as described above in Step D, (3.35 g, 13.7 mmol) and hydroxylamine hydrochloride (5.94 g, 85.5 mmol) in 95% EtOH (140 mL) at 60° C. was added KOH (11.9 g, 212 mmol) in MeOH (75 mL), dropwise over 30 min. The reaction mixture was stirred at 60° C. for 6 hours, then poured into H2O (200 mL) and extracted with CH2Cl2 (3×300 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with a gradient of hexane—20% to 40% EtOAc to yield the titled product.

Workup

  1. extractionextracted with CH2Cl2 (3×300 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography on silica
  6. washeluting with a gradient of hexane—20% to 40% EtOAc

Sources & evidence

ORD record
ord-de735f08f1724668b0fdf79b8064501e
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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