Hydroxyamine hydrochloride → HCID 73991942, compound

HRID 2249599Notes

Reaction equation

HRID 2249599 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][C:8](=O)[CH2:7][CH2:6][C:5]=2[N:4]=1.C([O-])(=O)C.[Na+].Cl.[NH2:20][OH:21]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][C:8](=[N:20][OH:21])[CH2:7][CH2:6][C:5]=2[N:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 100124622-methoxy-7,8-dihydro-5H-quinolin-6-one

Product 1

HCID 73991942HCID 73991942, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

2-Methoxy-7,8-dihydro-5H-quinolin-6-one (246 mg, synthesized according to J. Org. Chem. 1991, 56 (15), 4636) was dissolved in ethanol/water 1:1 (14 ml) and sodium acetate (600 mg) and hydroxylamine hydrochloride (482 mg) was added. The resulting suspension was heated to reflux for 4 hours until TLC analysis confirmed complete consumption of the starting tetrahydroquinolinone. The reaction mixture was poured into a mixture of ice, water and 1N NaOH (pH>10) and the aqueous layer was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried and evaporated to give a crude product. This was purified by flash chromatography (gradient of ethyl acetate in hexanes, 20% to 50%) to give the desired product as a mixture of (E/Z)-isomers (232 mg) as a yellow solid. Mp: 124-126° C. MS (ISP): 193.1 (MH+).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 4 hours until TLC analysis
  3. customconsumption of the starting tetrahydroquinolinone
  4. additionThe reaction mixture was poured into a mixture of ice, water and 1N NaOH (pH>10)
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with brine
  8. customdried
  9. customevaporated
  10. customto give a crude product
  11. customThis was purified by flash chromatography (gradient of ethyl acetate in hexanes, 20% to 50%)

Sources & evidence

ORD record
ord-d9953d236a8e4274b747fc05a6bc4ffa
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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