Hydroxyamine hydrochloride → HCID 86753147, compound

HRID 2395095Notes

Reaction equation

HRID 2395095 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH3:27])([CH3:26])[C:8]3[C:13]([O:14][C:15]=2[C:16]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:12]([CH:22]=O)[C:11]([O:24][CH3:25])=[CH:10][CH:9]=3.C([O-])(=O)C.[Na+].Cl.[NH2:34][OH:35]>CO.C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH3:27])([CH3:26])[C:8]3[C:13]([O:14][C:15]=2[C:16]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:12]([CH:22]=[N:34][OH:35])[C:11]([O:24][CH3:25])=[CH:10][CH:9]=3

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 53897197HCID 53897197, compound

Product 1

HCID 86753147HCID 86753147, compoundYield 95.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5 g (13.5 mmol) of methyl 3,6-dimethoxy-9,9-dimethyl-5-formylxanthene-4-acetate were dissolved in a mixture of 75 ml of methanol, 75 ml of THF and 20 ml of water. After the addition of 1.66 g of sodium acetate and 1.4 g of hydroxylamine hydrochloride the mixture was stirred at room temperature overnight and then diluted with 200 ml of water. The precipitated solid was filtered off, washed with water and dried, whereby 4.95 g of methyl 3,6-dimethoxy-9,9-dimethyl-5-[(hydroximino)methyl]xanthene-4-acetate were obtained as a white powder of m.p. 234°-236°; IR 1743, 1629, 1604, 1582, 1498 cm-1.

Workup

  1. filtrationThe precipitated solid was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-57843dbcd40d44c699a801b9a0716a8d
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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