Sodium Hydroxide → 5-(Propan-2-yl)azepan-2-one

HRID 851976Notes

Reaction equation

HRID 851976 reaction equation
[NH2:1]OS(O)(=O)=O.[CH:7]([CH:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1)([CH3:9])[CH3:8].[OH-].[Na+]>C(O)=O>[CH:7]([CH:10]1[CH2:15][CH2:14][NH:1][C:13](=[O:16])[CH2:12][CH2:11]1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 794884-Isopropylcyclohexanone

Product 1

HCID 123493095-(Propan-2-yl)azepan-2-one

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

To a solution of hydroxylamine-O-sulfonic acid (60.5 g, 535 mmol) in formic acid (320 ml) was added dropwise a solution of 4-isopropyl cyclohexanone (50.0 g, 357 mmol) in formic acid (110 ml) at r.t. under an argon atmosphere. The reaction mixture was refluxed for 3 h, cooled to r.t. and slowly treated with ice-water (550 ml). 10 N NaOH (1.1 liter) was added to adjust the pH to 8 and the resultant mixture was extracted with CHCl3 (4×). The combined organic extracts were washed with water, brine, dried (MgSO4), filtered and concentrated under reduced pressure. The light-brown solid was crystallized from n-heptane: 42.4 g (75%);

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. extractionthe resultant mixture was extracted with CHCl3 (4×)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe light-brown solid was crystallized from n-heptane

Sources & evidence

ORD record
ord-a93ebe11fb3e49c5b8aec4d3f1730def
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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