N-methylhydroxylamine hydrochloride → HCID 86605478, compound

HRID 2103016Notes

Reaction equation

HRID 2103016 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:21])=[C:7]2[C:15](=[C:16]([CH3:19])[C:17]=1[CH3:18])[O:14][C:10]1([CH2:13][CH2:12][CH2:11]1)[CH2:9][C:8]2=O)(=[O:3])[CH3:2].Cl.C[NH:24][OH:25].[C:26]([O-])(=O)C.[Na+]>CO.C(OCC)(=O)C>[C:1]([O:4][C:5]1[C:6]([CH3:21])=[C:7]2[C:15](=[C:16]([CH3:19])[C:17]=1[CH3:18])[O:14][C:10]1([CH2:11][CH2:12][CH2:13]1)[CH2:9][C:8]2=[N:24][O:25][CH3:26])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 69055283HCID 69055283, compound

Product 1

HCID 86605478HCID 86605478, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5,7,8-trimethyl-4-oxo-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-yl acetate (110 mg), N-methylhydroxylamine hydrochloride (64 mg), and sodium acetate (63 mg) in methanol (5 mL) was refluxed for 5 h. The mixture was diluted with ethyl acetate, washed with water and brine, dried and evaporated to give 100 mg of 4-(methoxyimino)-5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-yl acetate, which was used in the next step without further purification.

Workup

  1. temperaturewas refluxed for 5 h
  2. washwashed with water and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-e0213e4ba50b492daa53db45b1190176
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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