O-Methylhydroxylamine hydrochloride → HCID 178502629, compound

HRID 1952792Notes

Reaction equation

HRID 1952792 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=S)[C:6]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[C:5]2[C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21].Cl.[CH3:27][O:28][NH2:29]>C(O)C>[CH3:27][O:28][N:29]=[C:7]1[C:6]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:5]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[NH:8]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 23300103HCID 23300103, compound

Product 1

HCID 178502629HCID 178502629, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.42 g (1.07 mol) of 6-chloro-3-(p-chlorophenyl)-4-isopropoxycarbonylquinoline-2(1H)-thione (prepared according to methods from Examples 6, 7 and 8 described above, but using 5-chloroisatin and p-chlorophenyl acetic acid as starting materials) is dissolved in 10 ml of abs. ethanol and treated with 0.5 g of O-methylhydroxylamine hydrochloride. The reaction mixture is heated at reflux temperature for 3 hours. It is then concentrated under reduced pressure on a rotary evaporator, the residue is taken up in ethyl acetate, the organic phase is washed twice with water and, after drying by means of sodium sulfate, concentrated under reduced pressure on a rotary evaporator. The crude product obtained is purified by means of chromatography on silica gel (mobile phase: ethyl acetate/n-heptane=1/4). For fine purification, chromatography on ®Sephadex type LH-20 using methanol as the mobile phase is suitable.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux temperature for 3 hours
  3. concentrationIt is then concentrated under reduced pressure on a rotary evaporator
  4. washthe organic phase is washed twice with water
  5. dry with materialafter drying by means of sodium sulfate
  6. concentrationconcentrated under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-35d9183910bd450b98e7d09097d198af
Source dataset
uspto-grants-2000_09
Patent number
US06114349

Reaction notes

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