Hydrochloric Acid → HCID 11597826, compound

HRID 1785940Notes

Reaction equation

HRID 1785940 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[C@@H:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[OH-].[K+].C([OH:37])C.Cl>O.C(Cl)Cl>[C:9]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C@H:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:22]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([NH2:30])=[O:37])=[CH:27][CH:28]=2)=[O:31])[C@@H:14]([CH3:32])[CH2:13]1)(=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 11662235HCID 11662235, compound

Product 1

HCID 11597826HCID 11597826, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-cyanobenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (143 mg, 0.33 mmol) and potassium hydroxide (55 mg, 1.00 mmol)) were dissolved in water (150 mL), ethanol (3 mL) and heated to 70° C. for 4 h. The slurry was portioned between 1N HCl (until acidic) and methylene chloride. The organic layer was collected, concentrated and subjected to flash chromatography (EtOAc to 20% MeOH, EtOAc) to afford the title compound as a white solid.

Workup

  1. customThe organic layer was collected
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-185328c463a14c34a7f8240566847696
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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