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

HRID 1858166Notes

Reaction equation

HRID 1858166 reaction equation
CO[C:3](=[O:23])[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:22])[CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=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:23])=[C:16]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:15](=[O:22])[NH:14]2)=[CH:9][C:8]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 54055967Methyl 4-chloro-5-nitro-2-(2-(thiophen-2-yl)acetamido)benzoate

Product 1

HCID 547119717-chloro-4-hydroxy-6-nitro-3-(thiophen-2-yl)quinolin-2(1H)-oneYield 66.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-5-nitro-2-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester (130 mg in 4.0 mL dry tetrahydrofuran) at 0° C. was added dropwise a solution of sodium bis(trimethylsilyl)amide (0.92 mL of a 1.0M solution in tetrahydrofuran) and the mixture warmed to room temperature. After 3 hours, the reaction was quenched by the addition of 6N hydrochloric acid. The slurry was stirred for 10 minutes then filtered and washed with ice cold acetonitrile. The residue was dried in vacuo to give the title compound (79 mg).

Workup

  1. customthe reaction was quenched by the addition of 6N hydrochloric acid
  2. filtrationthen filtered
  3. washwashed with ice cold acetonitrile
  4. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-77b4e7fb5cd449d6b74d78aa7113f971
Source dataset
uspto-grants-2000_11
Patent number
US06150522

Reaction notes

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