Trifluoroacetic acid → 7-Chloro-6-nitro-4-(2-piperidin-2-yl-ethoxy)-3-thiophen-2-yl-1H-quinolin-2-one

HRID 1275592Notes

Reaction equation

HRID 1275592 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[Cl:30][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([O:16][CH2:15][CH2:14][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[C:18]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[C:19](=[O:31])[NH:20]2)=[CH:25][C:24]=1[N+:27]([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 536939232-[2-(7-Chloro-6-nitro-2-oxo-3-thiophen-2-yl-1,2-dihydro-quinolin-4-yloxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 98457627-Chloro-6-nitro-4-(2-piperidin-2-yl-ethoxy)-3-thiophen-2-yl-1H-quinolin-2-oneYield 68.4%

Reagents, catalysts & solvents 1

HCID 7519AnisoleCatalyst

Procedure

To a solution of 2-[2-(7-chloro-6-nitro-2-oxo-3-thiophen-2-yl-1,2-dihydro-quinolin-4-yloxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (45 mg in 2.0 mL methylene chloride) was added 2 drops of anisole followed by 1.0 mL of trifluoroacetic acid and the mixture stirred at room temperature. After 45 minutes the solvents were removed in vacuo and the resulting residue purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (25 mg).

Workup

  1. customAfter 45 minutes the solvents were removed in vacuo
  2. customthe resulting residue purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-3e4c438726394c52a2963ee08b0b78fa
Source dataset
uspto-grants-2000_12
Patent number
US06162813

Reaction notes

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