Hydrochloric Acid → 6-Hydroxy-2-phenylchroman-4-one Oxime

HRID 31248Notes

Reaction equation

HRID 31248 reaction equation
[OH-:1].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][C:7]2=O.Cl.[NH2:22]O.Cl>C(O)C.O>[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][C:7]2=[N:22][OH:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 443297Hydroxyamine hydrochloride2×HCID 27345806-Hydroxyflavanone

Product 1

HCID 734147306-Hydroxy-2-phenylchroman-4-one Oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Sodium hydroxide (122 mg) was added into a cooled solution of 6-hydroxyflavanone (2 g) and hydroxylamine hydrochloride (900 mg) in ethanol (5 ml) and water (2 ml). Resulting mixture was refluxed for 6 hours and hydroxylamine hydrochloride (450 mg) and sodium hydroxide (61 mg) were added after every 45 min. After cooling into room temperature water (23 ml) and concentrated hydrochloric acid (5.6 ml) were added into the mixture. Precipitate was filtered, washed with water and dried in vacuum. 1H-NMR (400 MHz, d6-DMSO): 11.3 (s, 1H), 9.11 (s, 1H), 7.50-7.48 (m, 2H), 7.43-7.33 (m, 3H), 7.21 (d, 1H, J 2.9 Hz), 6.80 (d, 1H, J 8.8 Hz), 6.72 (dd, 1H, J 2.9, 8.8 Hz), 5.07 (dd, 1H, J 3.2, 11.9 Hz), 3.28 (dd, 1H, J 3.2, 17.1 Hz), 2.64 (dd, 1H, J 11.9,17.1 Hz).

Workup

  1. customResulting mixture
  2. temperaturewas refluxed for 6 hours
  3. additionwere added into the mixture
  4. filtrationPrecipitate was filtered
  5. washwashed with water
  6. customdried in vacuum

Sources & evidence

ORD record
ord-68152485343046639c761c00120b42fd
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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