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

HRID 1857616Notes

Reaction equation

HRID 1857616 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[CH:37]=[CH:36][CH:35]=[C:34]([Br:38])[CH:33]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[Br:38][C:34]1[CH:33]=[C:32]([C:18]2[C:19](=[O:31])[NH:20][C:21]3[C:26]([C:17]=2[O:16][CH2:15][CH2:14][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]2)=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([Cl:30])[CH:22]=3)[CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 543094672-{2-[3-(3-Bromophenyl)-7-chloro-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 221300023-(3-bromophenyl)-7-chloro-6-nitro-4-(2-piperidin-2-yl-ethoxy)-1H-quinolin-2-oneYield 87.1%

Reagents, catalysts & solvents 1

HCID 7519AnisoleCatalyst

Procedure

To a solution of 2-{2-[3-(3-bromophenyl)-7-chloro-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (33 mg in 1.5 mL methylene chloride) was added 2 drops of anisole followed by 1.5 mL of trifluoroacetic acid and the mixture stirred at room temperature. After 1 hour 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 (24 mg).

Workup

  1. customAfter 1 hour 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-fb613d76bf0d4c73838efcd1806fd3fa
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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