Ethanol → HCID 10292998, compound

HRID 1795598Notes

Reaction equation

HRID 1795598 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][CH2:10][CH3:11])=[O:8])=[CH:5][CH:4]=1.[CH3:28]C1C=CC(C(OCC)=O)=C(NC2C(C)=CC3C(C)=CCC(C)(C)C=3C=2)C=1.C(O)C.[OH-].[K+]>O>[CH2:1]([N:2]([C:14]1[C:23]([CH3:24])=[CH:22][C:21]2[C:20]([CH3:25])=[CH:19][CH2:18][C:17]([CH3:26])([CH3:27])[C:16]=2[CH:15]=1)[C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12][CH:13]=1)[CH3:28]

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 22218302HCID 22218302, compoundHCID 22218312HCID 22218312, compound

Product 1

HCID 10292998HCID 10292998, 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 5 M 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 2 N 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, 6 H), 2.12 (s, 3 H), 2.14 (s, 3 H), 2.22 (d, 2 H, J=2.4 Hz), 3.32 (s, 3 H), 5.81 (s, 1 H), 6.52 (d, 2 H, J=7.5 Hz), 7.08 (s, 1 H), 7.19 (s, 1 H), 7.92 (d, 2 H, 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-1f6792f642a54dcba573fc63181640cf
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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