Sodium bis(trimethylsilyl)amide → 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-one

HRID 1857627Notes

Reaction equation

HRID 1857627 reaction equation
CO[C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH:11][C:12](=[O:22])[CH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Cl:10][C:7]1[CH:6]=[C:5]2[C:4]([C:3]([OH:23])=[C:13]([C:14]3[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([CH3:20])[CH:19]=3)[C:12](=[O:22])[NH:11]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 544849894-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester

Product 1

HCID 547315327-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-oneYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester (3.05 g in 20 mL dry tetrahydrofuran) at 0° C. was added dropwise a solution of sodium bis(trimethylsilyl)amide (20 mL of a 1.0M solution in tetrahydrofuran) and the mixture warmed to room temperature. After 2 hours, the reaction was cooled to 0° C. and quenched by the addition of 100 mL iced 6N hydrochloric acid. The slurry was stirred for 15 minutes then filtered and washed (2×) with ice cold acetonitrile. The residue was dried in vacuo overnight to give the title compound (2.3 g).

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. customquenched by the addition of 100 mL iced 6N hydrochloric acid
  3. filtrationthen filtered
  4. washwashed (2×) with ice cold acetonitrile
  5. customThe residue was dried in vacuo overnight

Sources & evidence

ORD record
ord-00d39333ee3e4aef8eaa52c49f4808be
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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