Hydroxyamine hydrochloride → HCID 85044904, compound

HRID 1986050Notes

Reaction equation

HRID 1986050 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=S)[CH:18]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:20])=[CH:5][CH:4]=1.Cl.[NH2:22][OH:23]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=[N:22][OH:23])[CH:18]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:20])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86002050HCID 86002050, compound

Product 1

HCID 85044904HCID 85044904, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-(4-Methoxy-phenyl)-8-methyl-chromene-4-thione (160.0 mg, 0.57 mmol) in 3.5 mL of pyridine was added 118.4 mg (1.70 mmol) of hydroxylamine hydrochloride. The solution was stirred at 110° C. for 1 h. The solvent was removed under vacuum and the residue was treated with ice. The resulting slurry was filtered. The filter cake was washed with H2O and then dried overnight under vacuum to afford 137.0 mg (85.7% yield) of desired compound I-23 as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 10.86 (s, 1H), 7.89 (d, 2H), 7.71 (d, 1H), 7.35 (d, 1H), 7.15 (t, 1H), 7.09 (d, 2H), 7.00 (s, 1H), 3.84 (s, 3H), 2.44 (s, 3H) ppm. LC/MS: 282.1 (M+H), 280.0 (M−H), HPLC/Method A (Rt 6.268 min, 95.4% purity).

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe residue was treated with ice
  3. filtrationThe resulting slurry was filtered
  4. washThe filter cake was washed with H2O
  5. customdried overnight under vacuum

Sources & evidence

ORD record
ord-f0ded93d715c4c2a9fb7c1efe261b7b8
Source dataset
uspto-grants-2009_06
Patent number
US07547794B2

Reaction notes

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