Hydroxyamine hydrochloride → HCID 73437173, compound

HRID 1700830Notes

Reaction equation

HRID 1700830 reaction equation
[OH2:1].O.O.C([O-])(=O)C.[Na+].Cl.[NH2:10]O.O=[C:13]([C:19]1[CH:20]=[CH:21][C:22]2[C:26]3[CH2:27][CH2:28][CH2:29][CH2:30][C:25]=3[O:24][C:23]=2[CH:31]=1)[CH2:14][CH2:15][C:16]([OH:18])=[O:17]>>[OH:1][N:10]=[C:13]([C:19]1[CH:20]=[CH:21][C:22]2[C:26]3[CH2:27][CH2:28][CH2:29][CH2:30][C:25]=3[O:24][C:23]=2[CH:31]=1)[CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 18318971HCID 18318971, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 73437173HCID 73437173, compoundYield 51%

Procedure

To a methanolic solution (50 mL) of 4-oxo-4-(6,7,8,9-tetrahydro-dibenzofuran-3-yl)-butyric acid (Keumi T., Saga H., Shimakawa S., et al., Fufui Daigaku, Kogakubu Seni Kogyu Kenkyu Shisetsu Hokoku, 1976;14:71-7 (mp 143-146° C.; mp 148.5-149.50° C. (lit.)) (0.6 g, 0.0022 mol) and sodium acetate trihydrate (0.9 g, 0.0066 mol) at room temperature with stirring was added an aqueous solution (10 mL) of hydroxylamine hydrochloride (0.31 g, 0.0044 mol). The resulting solution was heated to reflux for 4 hours. The solution was then cooled to room temperature and concentrated in vacuo. The residue was recrystallized form ethyl acetate/hexane (1:1) to yield the title compound (0.32 g, 51%) as a white solid; mp 164° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized form ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-f3e206a2ca6a426e874e92e73bceb442
Source dataset
uspto-grants-2002_02
Patent number
US06350885B1

Reaction notes

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