Hydroxyamine hydrochloride → HCID 178471206, compound

HRID 2383316Notes

Reaction equation

HRID 2383316 reaction equation
[C:1]([C:3]1[C:4]([CH3:28])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:7][CH2:6]2)#[N:2].Cl.[NH2:30][OH:31].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH:9]1[C:10]2[C:5](=[C:4]([CH3:28])[C:3]([C:1]([NH:30][OH:31])=[NH:2])=[CH:12][CH:11]=2)[CH2:6][CH2:7][N:8]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH3:20]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride4×HCID 516892Sodium Bicarbonate4×HCID 595910941,1-Dimethylethyl 6-cyano-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 178471206HCID 178471206, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1,1-dimethylethyl 6-cyano-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 26; 533 mg, 1.38 mmol), hydroxylamine hydrochloride (575 mg, 8.27 mmol) and sodium bicarbonate (695 mg, 8.27 mmol) in ethanol (15 ml) was stirred at 80° C. for 32 h. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalent of each) were added, and heating was continued at 80° C. overnight. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalent of each) were added, and heating was continued at 80° C. for 5.5 h. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalent of each) were added, and heating was continued at 80° C. overnight. The mixture was cooled to room temperature and the solid was filtered off and washed with ethanol. The filtrate and washings were combined, most of the solvent removed, and the residue dissolved in ethyl acetate. The solution was washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (500 mg) as a pale yellow foam.

Workup

  1. temperatureheating
  2. waitwas continued at 80° C. overnight
  3. temperatureheating
  4. waitwas continued at 80° C. for 5.5 h
  5. temperatureheating
  6. waitwas continued at 80° C. overnight
  7. temperatureThe mixture was cooled to room temperature
  8. filtrationthe solid was filtered off
  9. washwashed with ethanol
  10. customremoved
  11. dissolutionthe residue dissolved in ethyl acetate
  12. washThe solution was washed with brine
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f986d637a14f46a185fb6eafe5726ecc
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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