Methanol → 4-[(4,4-Dimethyl-2-isopropoxy-3,4-dihydro-7-quinolinyl)ethynyl]benzoic acid

HRID 52453Notes

Reaction equation

HRID 52453 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[NH:5][CH:4]([O:14][CH:15]([CH3:17])[CH3:16])[CH2:3]1.[Li+].[OH-:20].[CH3:21][OH:22]>O1CCCC1>[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][C:6]3[CH:11]=[CH:10][C:9]([C:21]([OH:22])=[O:20])=[CH:8][CH:7]=3)=[CH:9][CH:10]=2)[N:5]=[C:4]([O:14][CH:15]([CH3:16])[CH3:17])[CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 199637064,4-Dimethyl-2-isopropoxy-1,2,3,4-tetrahydro-7-ethynylquinoline2×

Product 1

HCID 199637234-[(4,4-Dimethyl-2-isopropoxy-3,4-dihydro-7-quinolinyl)ethynyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.0586 g (0.15 mmol) of 4,4-dimethyl-2-iso-propoxy-1,2,3,4-tetrahydro-7-ethynylquinoline (Compound 27) in 3.0 ml of tetrahydrofuran were added 1.0 ml (1.1 mmol) of 1.1M aqueous LiOH and 1.0 ml of methanol. The resulting solution was stirred at room temperature for 2 h. The reaction mixture was then concentrated and water was added to the residue. The aqueous layer was acidified to pH=1 with 10% HCl, and extracted with diethyl ether (2×). The organic layers were dried (MgSO4), filtered and concentrated to give the title compound as a solid.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additionwater was added to the residue
  3. extractionextracted with diethyl ether (2×)
  4. dry with materialThe organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-01d390c0e627418b8547b9e3e972342f
Source dataset
uspto-grants-1997_04
Patent number
US05616712

Reaction notes

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