Ethanol → HCID 11724509, compound

HRID 1166662Notes

Reaction equation

HRID 1166662 reaction equation
[CH3:1][N:2]([C:14]1[C:23]([CH3:24])=[CH:22][C:21]2[C:20]([CH3:25])=[CH:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=2[CH:15]=1)[C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][CH:4]=1.C(O)C.[OH-].[K+]>O>[CH3:1][N:2]([C:14]1[C:23]([CH3:24])=[CH:22][C:21]2[C:20]([CH3:25])=[CH:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=2[CH:15]=1)[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 22218312HCID 22218312, compound2×

Product 1

HCID 11724509HCID 11724509, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Following previously described General Procedure E, to a solution of ethyl 4-[methyl-(3,5,8,8-tetramethyl-7,8-dihydronaphthalen-2-yl)amino]benzoate (Compound 40, 0.05 g, 0.14 mmol) and 2 mL of absolute ethyl alcohol was added aqueous 5M KOH (0.3 mL). The resulting solution was heated in an 60° C. bath for 24 h. The solution was cooled to room temperature, diluted with water and washed once with 2:1 hexane:ethyl acetate solution, and the layers were separated. The aqueous layer was acidified with HCl 2N to pH=0-1 and the product extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, and filtered. The solvent was removed to give 0.042 g (92%) of the title compound as a dark green solid. PNMR (300 MHz, CDCl3) δ—1.24 (s, 6H), 2.12 (s, 3H), 2.14 (s, 3H), 2.22 (d, 2H, J=2.4 Hz), 3.32 (s, 3H), 5.81 (s, 1H), 6.52 (d, 2H, J=7.5 Hz), 7.08 (s, 1H), 7.19 (s, 1H), 7.92 (d, 2H, J=7.5 Hz).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. washwashed once with 2:1 hexane
  3. customethyl acetate solution, and the layers were separated
  4. extractionthe product extracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-d5ac75a5cd134010ab1385252af436f3
Source dataset
uspto-grants-2003_09
Patent number
US06613917B1

Reaction notes

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