Hydroxylamine → HCID 68871617, compound

HRID 1986352Notes

Reaction equation

HRID 1986352 reaction equation
[C:1]([CH2:3][CH:4]1[NH:23][C:7]2[CH:8]=[N:9][C:10]([O:12][C:13]3[CH:14]=[C:15]([NH:19][C:20](=[O:22])[CH3:21])[CH:16]=[CH:17][CH:18]=3)=[CH:11][C:6]=2[N:5]1[C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)#[N:2].[N:31]([O-:33])=O.[Na+].[NH2:35]O.[NH4+].[Cl-]>CO.O.Cl.O1CCOCC1.C(N(CC)CC)C>[NH2:2][C:1]1[C:3]([C:4]2[N:5]([C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)[C:6]3[CH:11]=[C:10]([O:12][C:13]4[CH:14]=[C:15]([NH:19][C:20](=[O:22])[CH3:21])[CH:16]=[CH:17][CH:18]=4)[N:9]=[CH:8][C:7]=3[N:23]=2)=[N:35][O:33][N:31]=1

Participants

10

Reactant 4

HCID 787HydroxylamineHCID 25517Ammonium Chloride2×HCID 23668193Sodium NitriteHCID 68871582HCID 68871582, compound

Product 1

HCID 68871617HCID 68871617, compoundYield 57%

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8471TriethylamineSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of the product from Step 4 (2.6 g, 6.5 mmol) in methanol (30 mL), water (20 mL) and 6M HCl (8 mL) was treated with NaNO2 (670 mg, 9.75 mmol) portionwise over 10 min then allowed to stir at rt for 1 h. The reaction mixture was poured into water and extracted with EtOAc. The organic phases were combined, washed with brine, dried (MgSO4), filtered and the filtrate concentrated to give a dark solid which was suspended in dioxane (20 mL) and treated with triethylamine (3 mL) and NH2OH (50% aqueous solution, 650 uL) and then heated to 90° C. for 2 h, then cooled to rt. The reaction mixture was poured into aq. NH4Cl and extracted with EtOAc. The organic phases were combined, washed with brine, dried (MgSO4), filtered and the filtrate concentrated to give a brown solid which was resuspended in dioxane (15 mL) and triethylamine (3 mL) and heated to 140° C. in a sealed tube for 3 h, then cooled to rt. The reaction mixture was poured into aq. NH4Cl and extracted with EtOAc. The organic phases were combined, washed with brine, dried (MgSO4), filtered and the filtrate concentrated to give the title compound (1.66 g, 57%) as a tan solid. MS (ES+) m/e 444 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customto give a dark solid which
  7. temperatureheated to 90° C. for 2 h
  8. temperaturecooled to rt
  9. extractionextracted with EtOAc
  10. washwashed with brine
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationthe filtrate concentrated
  14. customto give a brown solid which
  15. temperaturecooled to rt
  16. extractionextracted with EtOAc
  17. washwashed with brine
  18. dry with materialdried (MgSO4)
  19. filtrationfiltered
  20. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-608845755ac34e92a46dfebccc40c7b1
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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