Hydrochloric Acid → HCID 68918824, compound

HRID 1785985Notes

Reaction equation

HRID 1785985 reaction equation
C([O:4][CH2:5][C:6]([N:8]([C@H:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19](C(=O)C2C=C(C(F)(F)F)C=C(C(F)(F)F)C=2)[C@@H:18]([CH3:42])[CH2:17]1)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:7])(=O)C.[OH-].[K+].Cl>C(O)C.O>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([N:8]([C@H:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][C@@H:18]([CH3:42])[CH2:17]2)[C:6](=[O:7])[CH2:5][OH:4])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86601701HCID 86601701, compound

Product 1

HCID 68918824HCID 68918824, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-[{(2S,4R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}(4-chlorophenyl)amino]-2-oxoethyl acetate (500 mg, 0.82 mmol, 1 equ.) in ethanol (6 mL) and water (1 mL) was added potassium hydroxide (229 mg, 4.1 mmol, 5 equ.). The mixture was heated to 70° C. for 4 h. The mixture was neutralized with 1N aqueous HCl and extracted with ethyl acetate. The organic layer was separated, washed with a saturated aqueous solution of sodium bicarbonate and twice with brine, dried over sodium sulfate, filtered and concentrated to give crude N-(4-chlorophenyl)-2-hydroxy-N-[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide used as such in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium bicarbonate and twice with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bb6a2808ad384237b06f54398dc5aa61
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…