Hydroxyamine hydrochloride → HCID 59925106, compound

HRID 2300960Notes

Reaction equation

HRID 2300960 reaction equation
[CH2:1]([C:3]1([CH2:16][CH3:17])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5][C:4]1=O)[CH3:2].Cl.[NH2:19][OH:20]>N1C=CC=CC=1>[CH2:1]([C:3]1([CH2:16][CH3:17])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5][C:4]1=[N:19][OH:20])[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 13011008HCID 13011008, compound

Product 1

HCID 59925106HCID 59925106, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1,1-diethyl-7-methoxy-3,4-dihydro-1H-naphthalen-2-one (4.40 g, 18.96 mmol) in dry pyridine (20 mL) with the hydroxylamine hydrochloride salt (10.54 g, 151.7 mmol) was heated to 80 ° C. for one day. The mixture was cooled down to r.t., then the pyridine was removed under vaccum. The green gum was dissolved with AcOEt, washed with H2O, HCl 10%, H2O, brine, dried over MgSO4 and filtered through a small silica pad. The crude compound was used without any other purification (4.69 g, 100%). 1H NMR (CDCl3): 7.94 (1H, s, OH), 7.06 (1H, d, J=8 Hz, H5), 6.84 (1H, d, J=2.5 Hz, H8), 6.73 (1H, dd, J=2.5 and 8 Hz, H6), 3.83 (3H, s, OCH3), 2.80-2.75 (4H, m, PhCH2CH2), 2.08 (2H, m, CH2), 1.85 (2H, m, CH2), 0.68 (6H, t, J=7.5 Hz, CH3).

Workup

  1. customthe pyridine was removed under vaccum
  2. dissolutionThe green gum was dissolved with AcOEt
  3. washwashed with H2O, HCl 10%, H2O, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a small silica pad
  6. customThe crude compound was used without any other purification (4.69 g, 100%)

Sources & evidence

ORD record
ord-78b326568d8a4b22b29696d10ebcc46b
Source dataset
uspto-grants-2002_12
Patent number
US06498196B1

Reaction notes

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