Hydroxyamine hydrochloride → HCID 178452415, compound

HRID 1514236Notes

Reaction equation

HRID 1514236 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][C:7]=2[CH:20]=1)#[N:2].Cl.[NH2:22][OH:23].C(=O)(O)[O-].[Na+]>C(O)C>[OH:23][NH:22][C:1](=[NH:2])[C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:8][C:7]=2[CH:20]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 68467546HCID 68467546, compound

Product 1

HCID 178452415HCID 178452415, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 1,1-dimethylethyl 7-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 74) (2.016 g, 7.35 mmol), hydroxylamine hydrochloride (1.021 g, 14.70 mmol) and sodium bicarbonate (3.09 g, 36.7 mmol) in ethanol (30 ml) was heated at 60° C. overnight. The grey solid was removed by filtration and the filtrate evaporated. The resulting residue was dissolved in EtOAc, washed with water (3×20 ml), dried (MgSO4) and evaporated to give the title compound (1.77 g) as a white solid. MS (ES): C15H21N3O4 requires 307; found 308 [M+H]+.

Workup

  1. customThe grey solid was removed by filtration
  2. customthe filtrate evaporated
  3. dissolutionThe resulting residue was dissolved in EtOAc
  4. washwashed with water (3×20 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-50ca68de64b043388b6bb3a3f3bf92d8
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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