Hydroxyamine hydrochloride → HCID 178452412, compound

HRID 1514228Notes

Reaction equation

HRID 1514228 reaction equation
[C:1]([C:3]1[C:13]2[O:12][CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][C:7]=2[CH:6]=[CH:5][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[C:13]2[O:12][CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium BicarbonateHCID 54757009Tert-butyl 9-cyano-2,3-dihydrobenzo[F][1,4]oxazepine-4(5H)-carboxylate

Product 1

HCID 178452412HCID 178452412, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 1,1-dimethylethyl 9-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 64) (5.1 g, 18.59 mmol), hydroxylamine hydrochloride (2.58 g, 37.2 mmol) and sodium bicarbonate (7.81 g, 93 mmol) in ethanol (50 ml) was heated at 60° C. overnight. A further portion of hydroxylamine hydrochloride (1 g) was added and the reaction was heated at 60° C. overnight. The solid was filtered from the reaction mixture and the filtrate evaporated. The residue from the evaporation was dissolved in EtOAc, washed with water, dried over magnesium sulphate and evaporated. Trituration with ether to gave the title compound (3.94 g) as a white solid. MS (ES): C15H21N3O4 requires 307; found 308 [M+H]+.

Workup

  1. temperaturethe reaction was heated at 60° C. overnight
  2. filtrationThe solid was filtered from the reaction mixture
  3. customthe filtrate evaporated
  4. customThe residue from the evaporation
  5. dissolutionwas dissolved in EtOAc
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-c0d46a05387248558d159f24a420a158
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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