Hydroxyamine hydrochloride → HCID 178450882, compound

HRID 2383309Notes

Reaction equation

HRID 2383309 reaction equation
[CH2:1]([O:5][C:6](=[O:28])[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:20])[C:14]([C:18]#[N:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:2][CH2:3][CH3:4].Cl.[NH2:30][OH:31].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([O:5][C:6](=[O:28])[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:20])[C:14]([C:18]([NH:30][OH:31])=[NH:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium BicarbonateHCID 595910861,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 178450882HCID 178450882, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 18; 590 mg; 1.53 mmol), hydroxylamine hydrochloride (637 mg; 9.16 mmol) (769 mg; 9.16 mmol) followed by ethanol (15 ml) and the resulting suspension was stirred at 80° C. overnight. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalents of each) were added and the mixture stirred at 80° C. for ca. 14 h. The mixture was cooled to room temperature, and the precipitate was filtered off and the residue washed with ethanol. The combined filtrate and washings were evaporated in vacuo and the residue partitioned between water and ether. The phases were separated and the aqueous phase extracted twice with ether. The combined organic phases were dried over MgSO4 and concentrated in vacuo to give the title compound (547 mg).

Workup

  1. stirringthe mixture stirred at 80° C. for ca. 14 h
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationthe precipitate was filtered off
  4. washthe residue washed with ethanol
  5. customThe combined filtrate and washings were evaporated in vacuo
  6. customthe residue partitioned between water and ether
  7. customThe phases were separated
  8. extractionthe aqueous phase extracted twice with ether
  9. dry with materialThe combined organic phases were dried over MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-999670fbf3634ff79d7b6edd0196aada
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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