Isatin → HCID 178442075, compound

HRID 892469Notes

Reaction equation

HRID 892469 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].Cl.[NH2:13][OH:14]>C(O)C.O>[CH2:2]([C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[NH:1][C:2](=[O:3])[C:4]2=[N:13][OH:14])[CH2:4][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 7054IsatinHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178442075HCID 178442075, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of the isatin described in Example 10c (5.51 g) in ethanol (Z0 ml) was warmed slightly followed by addition of hydroxylamine hydrochloride (2.47 g) dissolved in water (10 ml). The mixture was warmed to about 80° with stirring for 10 minutes, followed by cooling to ambient temperature and stirring for 30 minutes. The precipitated yellow solid was filtered off, washed with water and dried to afford the title product (4.50 g, 76%) as a fluffy yellow powder: tlc, Rf =0.16, silica gel, ethyl acetate:hexane (2:3).

Workup

  1. temperaturewas warmed slightly
  2. temperatureThe mixture was warmed to about 80°
  3. stirringstirring for 30 minutes
  4. filtrationThe precipitated yellow solid was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-2c64c3e56f3046cb981f08f2503ca74f
Source dataset
uspto-grants-1992_06
Patent number
US05118688

Reaction notes

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