Lithium Hydroxide → HCID 89741115, compound

HRID 2206513Notes

Reaction equation

HRID 2206513 reaction equation
O=[C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Li+]>>[CH3:2][C:7]1[N:3]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:4]2[C:5]([C:6]=1[C:8]([OH:10])=[O:9])=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 117779426HCID 117779426, compound

Product 1

HCID 89741115HCID 89741115, compoundYield 88.9%

Procedure

To a solution of methyl 2-oxo-1-phenyl-1,2-dihydropyridine-4-carboxylate (272 mg, 1.03 mmol) in alcohol/water (v/v=1/1, 5 mL) was added lithium hydroxide (62 mg, 1.55 mmol), and the mixture was stirred at room temperature for 8 hours. The reaction mixture was concentrated, acidified by diluted aqueous hydrochloric acid (1 N, 5 mL) and extracted with ethyl acetate (2×10 ml). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 2-methyl-1-phenyl-1H-indole-3-carboxylic acid as white solid (115 mg, 44%). LRMS (M−H+) m/z: calcd for 251.09. found 251.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate (2×10 ml)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d6b0cc7270a4445fbed3fe9d1e5c1c7c
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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