Hydroxyamine hydrochloride → HCID 178426655, compound

HRID 2037329Notes

Reaction equation

HRID 2037329 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][C:5]1([CH3:22])[O:9][CH:8]([CH2:10][O:11][C:12]2[C:19]([CH3:20])=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[CH3:21])[CH2:7][O:6]1>CO>[CH3:4][C:5]1([CH3:22])[O:9][CH:8]([CH2:10][O:11][C:12]2[C:19]([CH3:20])=[CH:18][C:15]([C:16]([NH:2][OH:3])=[NH:17])=[CH:14][C:13]=2[CH3:21])[CH2:7][O:6]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66692495Rac-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3,5-dimethyl-benzonitrile

Product 1

HCID 178426655HCID 178426655, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of potassium tert.-butylate (6.18 g, 55.1 mmol) in methanol (125 mL), hydroxylamine hydrochloride (5.74 g, 82.7 mmol) is added. To this solution, a solution of rac-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3,5-dimethyl-benzonitrile (7.20 g, 27.6 mmol) in methanol (40 mL) is added. The mixture is refluxed for 72 h before the solvent is removed in vacuo. The residue is purified by prep. HPLC (XBridge Prep C18, 30×75 mm, 5 μm, 2-95% acetonitrile in water containing 0.5% sat. aq. NH3) to give the title compound (4.85 g) as a pale yellow solid; LC-MS: tR=0.67 min, [M+1]+=295.06; 1H NMR (CDCl3): δ 1.43 (s, 3H), 1.48 (s, 3H), 2.29 (s, 6H), 3.76-3.81 (m, 1H), 3.83-3.88 (m, 1H), 3.93-3.99 (m, 1H), 4.17-4.23 (m, 1H), 4.47-4.54 (m, 1H), 5.02 (s br, 1H), 7.28 (s, 2H).

Workup

  1. temperatureThe mixture is refluxed for 72 h before the solvent
  2. customis removed in vacuo
  3. customThe residue is purified by prep

Sources & evidence

ORD record
ord-7b0f35dc65864258849f51a9ed3ea000
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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