Potassium Carbonate → HCID 178437966, compound

HRID 2114622Notes

Reaction equation

HRID 2114622 reaction equation
[ClH:1].[NH2:2][OH:3].C(=O)([O-])[O-].[K+].[K+].[Cl:10][C:11]1[CH:12]=[C:13]([CH:27]=[C:28](Cl)[CH:29]=1)[O:14][C:15]1[C:16]([CH2:25][CH3:26])=[N:17][N:18]([CH2:22][C:23]#[N:24])[C:19]=1[CH2:20][CH3:21]>CO.O>[Cl:1][C:28]1[CH:27]=[C:13]([CH:12]=[C:11]([Cl:10])[CH:29]=1)[O:14][C:15]1[C:16]([CH2:25][CH3:26])=[N:17][N:18]([CH2:22][C:23](=[NH:24])[NH:2][OH:3])[C:19]=1[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 9880293HCID 9880293, compound

Product 1

HCID 178437966HCID 178437966, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (1.1 g, 15.8 mmol) and potassium carbonate (2.1 g, 15.2 mmol) were added to a suspension of the nitrile (1 g, 3.1 mmol) of Example 4 in a mixture of methanol (25 ml) and water (10 ml) which was then heated under reflux for 3 days. After cooling, the mixture was extracted with dichloromethane (2×250 ml) and the combined organic layers were washed with brine (100 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to afford the product as a white solid (1.1 g), m.p. 128-130° C.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 3 days
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with dichloromethane (2×250 ml)
  5. washthe combined organic layers were washed with brine (100 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4604d965c340429fb6a181ff1238d0a9
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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