Hydroxyamine hydrochloride → HCID 59925101, compound

HRID 2300965Notes

Reaction equation

HRID 2300965 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.Cl.[NH2:17][OH:18]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[N:17][OH:18])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one

Product 1

HCID 59925101HCID 59925101, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

7-Methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (used as a crude from example 1, step1, 128.8 g, 0.63 mol) and hydroxylamine hydrochloride (350 g, 5.04 mol) in pyridine (360 ml) were heated up to 80° C. The reaction mixture was stirred for 15 h at 80-90° C. Pyridine was removed under reduced pressure. The residue was partitioned between ethylacetate (2.5 l) and water (1 l). Water layer was separated and washed with ethyl acetate (1 l). Ethyl acetate solution was washed with 10% aq. KHSO4 (1 l), dried over Na2SO4. Ethyl acetate was removed under reduced pressure and the residue was crystallized from acetone to give 101.2 g of target compound. Mother liquid was concentrated to dryness and crystallized from acetone to give second crop (11.4 g). 112.6 g (82%) of the desired product was obtained. 1H NMR (CDCl3), d 9.15 (s, 1H), 7.06 (d, 1H, J=7.4 Hz) 6.92 (1H, d, J=2.4 Hz), 6.75 (dd, 1H, J=7.4 and 2.4 Hz), 3.82 (s, 3H), 2.78-2.95 (m, 4H), 1.5 (s, 6H).

Workup

  1. customPyridine was removed under reduced pressure
  2. customThe residue was partitioned between ethylacetate (2.5 l) and water (1 l)
  3. customWater layer was separated
  4. washwashed with ethyl acetate (1 l)
  5. washEthyl acetate solution was washed with 10% aq. KHSO4 (1 l)
  6. dry with materialdried over Na2SO4
  7. customEthyl acetate was removed under reduced pressure
  8. customthe residue was crystallized from acetone
  9. customto give 101.2 g of target compound
  10. concentrationMother liquid was concentrated to dryness
  11. customcrystallized from acetone
  12. customto give second crop (11.4 g)

Sources & evidence

ORD record
ord-94c4317e854d4c38b966edf0ed15e9ee
Source dataset
uspto-grants-2002_12
Patent number
US06498196B1

Reaction notes

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