Sodium bis(trimethylsilyl)amide → 6-allyl-7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-one

HRID 1858086Notes

Reaction equation

HRID 1858086 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([CH2:10][CH:11]=[CH2:12])[C:7]([Cl:13])=[CH:6][C:5]=1[NH:14][C:15](=[O:25])[CH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[CH2:10]([C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][C:7]=1[Cl:13])[NH:14][C:15](=[O:25])[C:16]([C:17]1[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=1)=[C:3]2[OH:2])[CH:11]=[CH2:12]

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 542443075-Allyl-4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester

Product 1

HCID 547112376-allyl-7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-oneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-allyl-4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester (1.4 g in 40 mL dry tetrahydrofuran) at 0° C. was added dropwise a solution of sodium bis(trimethylsilyl)amide (9.8 mL of a 1.0M solution in tetrahydrofuran) and the mixture warmed to room temperature. After 4 hours, the reaction was cooled to 0° C. and quenched by the addition of of 200 mL iced 6N hydrochloric acid. The slurry was stirred for 15 minutes then filtered and washed sequentially with ice water (500 mL), cold hexane (200 mL) and cold toluene (100 mL). The residue was dried in vacuo to give the title compound (960 mg).

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. customquenched by the addition of of 200 mL iced 6N hydrochloric acid
  3. filtrationthen filtered
  4. washwashed sequentially with ice water (500 mL), cold hexane (200 mL) and cold toluene (100 mL)
  5. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-46ccd0b5b61e471dace5e730d606d517
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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