O-Methylhydroxylamine hydrochloride → HCID 76614993, compound

HRID 2102994Notes

Reaction equation

HRID 2102994 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][CH2:9][C:6]1([CH2:8][CH2:7]1)[C:5]2=O.Cl.[CH3:18][O:19][NH2:20]>N1C=CC=CC=1>[CH3:18][O:19][N:20]=[C:5]1[C:6]2([CH2:8][CH2:7]2)[CH2:9][O:10][C:11]2[C:4]1=[CH:3][C:2]([OH:1])=[C:13]([CH3:14])[C:12]=2[CH3:15]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 69053342HCID 69053342, compound

Product 1

HCID 76614993HCID 76614993, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
200 °C

Procedure

A solution of 6-hydroxy-7,8-dimethyl-4H-spiro[chromene-3, 1′-cyclopropan]-4-one (10 mg), prepared as described above, methoxyamine hydrochloride (110 mg) in pyridine (3 mL) was stirred in a microwave reaction tube (200° C., 30 min). After cooling down, the mixture was partitioned between water and ethylacetate, and the organic layer was washed with dil. HCl, dried, and evaporated. The residue was purified by silica gel column eluting with 15% EtOAc in hexane to give a 3.6 mg of 6-hydroxy-7,8-dimethylspiro[chroman-3,1′-cyclopropan]-4-one O-methyl oxime.

Workup

  1. temperatureAfter cooling down
  2. customthe mixture was partitioned between water and ethylacetate
  3. washthe organic layer was washed with dil. HCl
  4. customdried
  5. customevaporated
  6. customThe residue was purified by silica gel column
  7. washeluting with 15% EtOAc in hexane

Sources & evidence

ORD record
ord-8611bcd64bef4016a9d84e067fe5b1f7
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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