Sodium Bicarbonate → HCID 68680210, compound

HRID 1444486Notes

Reaction equation

HRID 1444486 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:15]=[CH:16][C:17]([OH:35])([C:31]([F:34])([F:33])[F:32])[CH2:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=2[O:29][CH3:30])([CH3:21])[CH3:20])[N:6]=1)=[O:4].C(=O)(O)[O-].[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:15][CH:16]2[C:27]3[C:22](=[C:23]([O:29][CH3:30])[C:24]([F:28])=[CH:25][CH:26]=3)[C:19]([CH3:21])([CH3:20])[CH2:18][C:17]2([OH:35])[C:31]([F:32])([F:33])[F:34])[N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 68680857HCID 68680857, compound

Product 1

HCID 68680210HCID 68680210, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

5-[4-(3-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]-quinoline-2-carboxylic acid methyl ester (120 mg, 0.243 mmol) is dissolved in 2.0 ml of dichloromethane. Titanium tetrachloride (1 M solution in dichloromethane, 0.73 ml, 0.73 mmol) is added in drops within 15 minutes at −30° C. Then, the reaction mixture is allowed to stir for 3 hours at −30° C. to −15° C. By adding saturated sodium bicarbonate solution at −30° C., the reaction is brought to a halt. It is extracted with ethyl acetate, the combined organic phases are washed with water and saturated sodium chloride solution. After drying on sodium sulfate and after the solvent is removed in a vacuum as well as subsequent purification on silica gel with dichloromethane/methanol (0-3% methanol), 70 mg (58% of theory) of the product is obtained.

Workup

  1. extractionIt is extracted with ethyl acetate
  2. washthe combined organic phases are washed with water and saturated sodium chloride solution
  3. customAfter drying on sodium sulfate
  4. customafter the solvent is removed in a vacuum as
  5. customwell as subsequent purification on silica gel with dichloromethane/methanol (0-3% methanol), 70 mg (58% of theory) of the product
  6. customis obtained

Sources & evidence

ORD record
ord-1d94b67854494572a9e51ddfe99b5c2c
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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