Hydroxyamine hydrochloride → HCID 178501076, compound

HRID 528702Notes

Reaction equation

HRID 528702 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[N:19]N(C)C)=[O:12])[CH2:7][CH2:6]1)=[O:4].C([O-])(=O)C.[Na+].Cl.NO>CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[O:12][N:19]=[C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:13]=23)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 178501136HCID 178501136, compound

Product 1

HCID 178501076HCID 178501076, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of trans-4-[2-(dimethyl-hydrazono)-cyclohexanecarbonyl]-cyclohexanecarboxylic acid methyl ester (0.95 g, 3.1 mmol), sodium acetate (0.28 g, 3.4 mmol) and hydroxylamine hydrochloride (0.24 g, 3.4 mmol) in methanol (15 ml) was stirred at room temperature for 16 h. The reaction mixture was partitioned between ethyl acetate (100 ml) and water (50 ml). The layers were separated. The aqueous layer was extracted with two 100-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue (0.88 g) was dissolved in toluene (15 ml). After addition of a catalytic amount of toluene-4-sulfonic acid monohydrate the mixture was heated at reflux for 3 h. The solvent was evaporated. Purification with n-heptane/ethyl acetate as eluent gave the title compound (0.58 g, 72%) with a regioisomeric purity of approx. 90% according to 13C-NMR. MS m/e: 264 ([M+H]+)

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (100 ml) and water (50 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with two 100-ml portions of ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue (0.88 g) was dissolved in toluene (15 ml)
  7. additionAfter addition of a catalytic amount of toluene-4-sulfonic acid monohydrate the mixture
  8. temperaturewas heated
  9. temperatureat reflux for 3 h
  10. customThe solvent was evaporated
  11. customPurification with n-heptane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-7a8f03e8ee8f4f0ba63e1d07ec0dbf00
Source dataset
uspto-grants-2016_05
Patent number
US09346824B2

Reaction notes

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