Lithium Hydroxide → 1-Acetyl-6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

HRID 2365303Notes

Reaction equation

HRID 2365303 reaction equation
C[O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=2)[N:6]1[C:16](=[O:18])[CH3:17])=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[C:16]([N:6]1[C:7]2[C:12](=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=2)[CH2:13][CH2:14][CH:5]1[C:3]([OH:4])=[O:2])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 596259921-Acetyl-6-bromo-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester

Product 1

HCID 596259471-Acetyl-6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of compound 25b (116 mg, 0.37 mmol) in THF/MeOH/H2O (2/2/2 mL) was added LiOH (62 mg, 1.48 mmol). The reaction mixture was stirred at room temperature for 3 h. The resultant mixture was concentrated under reduced pressure, partitioned between CH2Cl2 and H2O, and the aqueous phase was brought to pH 5 by the addition of 2N HCl (aq). The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude compound 25c, which was used in the next step without further purification. LC/MS m/z 298.0 (M+H+), 300.0 (M+2H+).

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. custompartitioned between CH2Cl2 and H2O
  3. additionthe aqueous phase was brought to pH 5 by the addition of 2N HCl (aq)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c8796ab14b0b4b10b4b2a78cb5218ec0
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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