Hydroxyamine hydrochloride → 1-(2,6-Dihydroxyphenyl)-2-methyl-1-propanone oxime

HRID 527533Notes

Reaction equation

HRID 527533 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=O)[CH:10]([CH3:12])[CH3:11].Cl.[NH2:15][OH:16]>N1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[N:15][OH:16])[CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochloride2×HCID 134833211-(2,6-Dihydroxyphenyl)-2-methyl-1-propanone2×

Product 1

HCID 1363786541-(2,6-Dihydroxyphenyl)-2-methyl-1-propanone oximeYield 82.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(2,6-dihydroxyphenyl)-2-methyl-1-propanone (Intermediate 37, 416 mg) was dissolved in pyridine (2.0 ml) and hydroxylamine hydrochloride (209 mg, 3.0 mmol) was added. The reaction mixture was then stirred at room temperature overnight. After night, additional hydroxylamine hydrochloride (64 mg, 0.92 mmol) was added and the mixture was heated at 100° C. for 3 hours. After removal of the volatiles, the crude was treated with water and extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound (370 mg).

Workup

  1. waitAfter night
  2. temperaturethe mixture was heated at 100° C. for 3 hours
  3. customAfter removal of the volatiles
  4. additionthe crude was treated with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe gathered organic layers were dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-14d6092fb08e4a45b5222e0f7b9b2715
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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