Hydroxylamine → 7-nitro-3,4-dihydro-2H-naphthalen-1-one oxime

HRID 470126

Reaction equation

HRID 470126 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:15][OH:16]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[N:15][OH:16])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 384457-Nitro-1-tetralone

Product 1

HCID 3000317-nitro-3,4-dihydro-2H-naphthalen-1-one oximeYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 7-nitro-3,4-dihydro-2H-naphthalen-1-one (500 mg, 2.62 mmol) in pyridine (2 mL) was added hydroxylamine solution (1 mL, ˜50% solution in water). The reaction was stirred at room temperature for 1 h, then concentrated and purified by column chromatography (10-50% ethyl acetate-hexanes) to yield 7-nitro-3,4-dihydro-2H-naphthalen-1-one oxime (471 mg, 88%). HPLC ret. time 2.67 min, 10-99% CH3CN, 5 min run; ESI-MS 207.1 m/z (MH+).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography (10-50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-59d88fea95774bfdbbb218255e86ce5e
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Linked notes

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