Lithium Hydroxide → HCID 18931447, compound

HRID 1598970Notes

Reaction equation

HRID 1598970 reaction equation
[CH3:1][C:2]1([CH3:32])[C:11]2[C:6](=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[N:5]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)[CH2:4][CH2:3]1.CC1(C)C2C(=CC(/C=C/C3C=CC(C([O-])=O)=CC=3)=CC=2)N(C2C=CC(C)=CC=2)CC1.[Li+].[OH-]>O1CCCC1.CO>[CH3:1][C:2]1([CH3:32])[C:11]2[C:6](=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[N:5]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 18931446HCID 18931446, compoundHCID 86752403HCID 86752403, compound

Product 1

HCID 18931447HCID 18931447, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.033 g (0.08 mmol) of ethyl (E)-4-(2-(4,4-dimethyl-1,2,3,4-tetrahydro-N-(4-methylphenyl)quinolin-7-yl)ethenyl)benzoate (Compound 13) in 4.0 mL of tetrahydrofuran and 1.0 mL of methanol was added 1.0 mL (0.6 mmol) of 0.6M aqueous LiOH. The resulting solution was stirred at room temperature for 48 hours. The mixture was concentrated in vacuo, water was added, and the mixture was extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo, followed by recrystallization in acetonitrile to give the title compound as a solid. PNMR (300 MHz, DMSO) d 1.30 (6 H, s), 1.77 (2 H, t, J=6.0 Hz), 2.30 (3 H, s), 3.54 (2 H, t, J=6.0 Hz), 6.69 (1 H, s), 6.95-7.28 (8 H, m), 7.46 (2 H, d, J=8.4 Hz), 7.96 (2 H, d, J=8.4 Hz).

Workup

  1. concentrationThe mixture was concentrated in vacuo, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (2x)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customfollowed by recrystallization in acetonitrile

Sources & evidence

ORD record
ord-d63acec170c64a2b85fd3cb82f7af124
Source dataset
uspto-grants-1998_04
Patent number
US05739338

Reaction notes

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