O-Methylhydroxylamine hydrochloride → HCID 76614995, compound

HRID 2103036Notes

Reaction equation

HRID 2103036 reaction equation
[CH2:1]([C:3]1[C:15]([OH:16])=[C:14]([CH3:17])[C:13]([CH3:18])=[C:12]2[C:4]=1[C:5](=O)[CH2:6][C:7]1([O:11]2)[CH2:10][CH2:9][CH2:8]1)[CH3:2].Cl.[CH3:21][O:22][NH2:23]>N1C=CC=CC=1>[CH3:21][O:22][N:23]=[C:5]1[C:4]2[C:12](=[C:13]([CH3:18])[C:14]([CH3:17])=[C:15]([OH:16])[C:3]=2[CH2:1][CH3:2])[O:11][C:7]2([CH2:10][CH2:9][CH2:8]2)[CH2:6]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 69053766HCID 69053766, compound

Product 1

HCID 76614995HCID 76614995, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-ethyl-6-hydroxy-7,8-dimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one (0.51 g) in 9 mL of pyridine was added methoxyamine hydrochloride (0.82 g). The reaction mixture was allowed to stir at room temperature overnight. The mixture was extracted with ethyl acetate, washed with 1N HCl, and concentrated in vacuo to give 5-ethyl-6-hydroxy-7,8-dimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one O-methyloxime, 1H-NMR (300 MHz, CDCl3) δ=4.58 (s, 1H, 4.01 (s, 3H), 3.05 (m, 2H), 3.02 (s, 2H), 2.20 (s, 3H), 2.17 (s, 3H), 2.10-1.60 (m, 6H), 1.24 (t, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ=151.0, 147.4, 146.3, 125.8, 124.6, 124.3, 115.3, 76.9, 61.9, 33.9, 33.4, 21.2, 13.6, 12.7, 12.3, 12.1 ppm. MS: (m/z)=290.1 (M+H+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with 1N HCl
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44e2fca42b834b19bb89c832dbf6b384
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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