Hydroxyamine hydrochloride → HCID 178426655, compound

HRID 1958780Notes

Reaction equation

HRID 1958780 reaction equation
CC([O-])(C)C.[K+].Cl.[NH2:8][OH:9].[CH3:10][C:11]1([CH3:28])[O:15][CH:14]([CH2:16][O:17][C:18]2[C:25]([CH3:26])=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=2[CH3:27])[CH2:13][O:12]1>CO>[CH3:10][C:11]1([CH3:28])[O:15][CH:14]([CH2:16][O:17][C:18]2[C:25]([CH3:26])=[CH:24][C:21]([C:22]([NH:8][OH:9])=[NH:23])=[CH:20][C:19]=2[CH3:27])[CH2:13][O:12]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 23665647Potassium tert-butoxideHCID 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 MeOH (125 mL), hydroxylamine hydrochloride (5.74 g, 82.7 mmol) was 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 MeOH (40 mL) was added. The mixture was refluxed for 72 h before the solvent was removed in vacuo. The residue was 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 as a pale yellow solid (4.85 g). LC-MS: tR=0.67 min, [M+1]+=295.06; 1H NMR (CDCl3): δ1.43 (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 (br s, 1H), 7.28 (s, 2H).

Workup

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

Sources & evidence

ORD record
ord-eb3fade749ab4d08a0fe130f9f272109
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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