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

HRID 1858063Notes

Reaction equation

HRID 1858063 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[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>[Cl:13][C:7]1[CH:6]=[C:5]2[C:4]([C:3]([OH:2])=[C:16]([C:17]3[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=3)[C:15](=[O:25])[NH:14]2)=[CH:9][C:8]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 543134564-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-nitro-benzoic acid methyl ester

Product 1

HCID 547112387-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-oneYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-nitrobenzoic acid methyl ester (1.17 g in 10 mL dry tetrahydrofuran) at 0° C. was added dropwise a solution of sodium bis(trimethylsilyl)amide (7.8 mL of a 1.0M solution in tetrahydrofuran) and the mixture warmed to room temperature. After 2 hours, the reaction was quenched by the addition of 100 mL iced 6N hydrochloric acid. The slurry was stirred for 10 minutes then filtered and washed (2×) with ice water and then cold acetonitrile. The residue was dried overnight at 45° C. to give the title compound (970 mg).

Workup

  1. customthe reaction was quenched by the addition of 100 mL iced 6N hydrochloric acid
  2. filtrationthen filtered
  3. washwashed (2×) with ice water
  4. customThe residue was dried overnight at 45° C.

Sources & evidence

ORD record
ord-f14a60757f4d425a904ec1430cd74a2e
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

Loading…