Hydroxyamine hydrochloride → HCID 178452417, compound

HRID 1514199Notes

Reaction equation

HRID 1514199 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]2[CH2:7][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=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:20]=[CH:19][C:6]2[CH2:7][N:8]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 684679231,1-Dimethylethyl 8-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Product 1

HCID 178452417HCID 178452417, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1,1-dimethylethyl 8-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 32) (0.195 g, 0.711 mmol), hydroxylamine hydrochloride (0.099 g, 1.422 mmol) and sodium bicarbonate (0.299 g, 3.55 mmol) in ethanol (5 ml) was stirred and heated at 60° C. for 3 hours. The reaction mixture was cooled, evaporated and dissolved in EtOAc/water (40 ml of each, some warming needed) and the organics dried (magnesium sulphate) and evaporated to give the title compound (210 mgs) as a white solid. MS (ES) C15H21N3O4 requires 307; found 308 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated
  3. dissolutiondissolved in EtOAc/water (40 ml of each, some warming
  4. dry with materialorganics dried (magnesium sulphate)
  5. customevaporated

Sources & evidence

ORD record
ord-829bbaad66a74d60bf89870281ab058c
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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