Hydrochloric Acid → HCID 178526332, compound

HRID 1678792Notes

Reaction equation

HRID 1678792 reaction equation
O1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:18]4=[N:28][N:29]=[C:30]([C:31]5[N:32]=[CH:33][NH:34][CH:35]=5)[N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1.Cl.Cl.[NH2:38][OH:39]>O1CCOCC1.O>[NH:34]1[CH:35]=[C:31]([C:30]2[N:17]3[C:18]([C:19]4[CH:20]=[C:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:12]([C:9]5[CH:8]=[CH:7][C:6]([CH:2]=[N:38][OH:39])=[CH:11][CH:10]=5)=[N:13][C:14]=4[CH:15]=[CH:16]3)=[N:28][N:29]=2)[N:32]=[CH:33]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 178420050HCID 178420050, compound

Product 1

HCID 178526332HCID 178526332, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 22-1 (0.8 g, 1.7 mmol) in 1,4-dioxane (3 ml) was added 3N HCl (1.1 ml, 3.4 mmol) dropwise. After stirring for 10 min the solution was treated with hydroxylamine hydrochloride (0.5 g, 6.9 mmol) in water (0.5 ml). The mixture was stirred for 1 h and was then quenched with NaHCO3(s) until pH=8. Upon solvent removal the residue was taken up in water, filtered, and dried azeotropically with toluene to afford 22-2 as a solid.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. customwas then quenched with NaHCO3(s) until pH=8
  3. customUpon solvent removal the residue
  4. filtrationfiltered
  5. dry with materialdried azeotropically with toluene

Sources & evidence

ORD record
ord-85ad4a3481584aecb50c42e2c4f66184
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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