Hydroxyamine hydrochloride → HCID 172982812, compound

HRID 1986482Notes

Reaction equation

HRID 1986482 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:7]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:6]2[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)#[N:2].Cl.[NH2:34][OH:35].CC(C)([O-])C.[Na+]>C(O)C>[NH2:2]/[C:1](=[N:34]\[OH:35])/[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:7]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:6]2[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 23676156Sodium t-butoxideHCID 86605654HCID 86605654, compound

Product 1

HCID 172982812HCID 172982812, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of tert-butyl [6-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (3.0 g, 7.0 mmol), hydroxylamine hydrochloride (0.73 g, 11 mmol) and ethanol (75 ml) was added sodium tert-butoxide (1.2 g, 11 mmol), and the mixture was stirred at 70° C. for 6 hrs. The precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate-tetrahydrofuran and water and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give tert-butyl [6-[(Z)-amino(hydroxyimino)methyl]-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (2.5 g, yield 79%) as a white powder.

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate-tetrahydrofuran and water
  4. washthe organic layer was washed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e70fddbd6ebf42e3863a2f326732d4e8
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

Loading…