Potassium Carbonate → tert-Butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 505571Notes

Reaction equation

HRID 505571 reaction equation
C([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][N:10]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][N:10]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68428249HCID 68428249, compound

Product 1

HCID 53432595tert-Butyl 5-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of t-butyl 5-(acetyloxy)-3,4-dihydroquinoline-1(2H)-carboxylate (770 mg, 2.64 mmol) in 10 mL of MeOH was added potassium carbonate (365 mg, 2.64 mmol), and the resulting mixture was stirred for 2 hours at room temperature and then filtered and concentrated in vacuo. The crude material was purified on a silica gel column (5% to 35% EtOAc/hexanes) to afford the desired product.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified on a silica gel column (5% to 35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-583053a79d8346b98ee1c27a8dc300ec
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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