Ammonium Acetate → 1-(2-(4-aminocyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

HRID 39704Notes

Reaction equation

HRID 39704 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:23])=[CH:8][C:9](=[O:22])[N:10]2[CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)=[CH:5][CH:4]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:30].[Na+]>C(O)C>[NH2:30][CH:18]1[CH2:19][CH2:20][CH:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[C:7]([CH3:23])=[CH:8][C:9]2=[O:22])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride2×HCID 593978507-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one

Product 1

HCID 593982031-(2-(4-aminocyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.5 mL of an ethanol solution containing 10 mg of 7-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one, 3.7 mg of ammonium acetate and 15 mg of molecular sieves 3A were added at room temperature, the mixture was stirred for 1 hour, then thereto was added 5.0 mg of sodium cyanoborohydride, and the mixture was stirred at the same temperature for 4 hours and 30 minutes. Thereto was further added 3.0 mg of sodium cyanoborohydride, and the mixture was stirred for 30 minute, and then left to stand overnight. The solvent was removed under reduced pressure, water and ethyl acetate were added thereto, the reaction mixture was adjusted to pH 3 to 4 (pH test paper) with 2.0 mol/L hydrochloric acid, and the aqueous layer was separated. The aqueous layer was added with ethyl acetate, and the resultant solution was adjusted to pH 8 to 9 (pH test paper) with a 2.0 mol/L aqueous sodium hydroxide solution. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 6.0 mg of a colorless oily substance, 1-(2-(4-aminocyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one.

Workup

  1. additionwere added at room temperature
  2. stirringthe mixture was stirred at the same temperature for 4 hours and 30 minutes
  3. stirringthe mixture was stirred for 30 minute
  4. waitleft
  5. waitto stand overnight
  6. customThe solvent was removed under reduced pressure, water and ethyl acetate
  7. additionwere added
  8. customthe aqueous layer was separated
  9. additionThe aqueous layer was added with ethyl acetate
  10. customThe organic layer was separated
  11. washwashed with an aqueous saturated sodium chloride solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-114aad7dfaca470c93fbab9c2ae4477e
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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