Pyridine → HCID 7667367, compound

HRID 1372429Notes

Reaction equation

HRID 1372429 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Cl[S:12]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[CH2:18]2)(=[O:14])=[O:13].N1C=CC=CC=1>ClCCl>[N:1]1([S:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18]3)(=[O:13])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 694601,2,3,4-TetrahydroquinolineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 7667367HCID 7667367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,2,3,4-tetrahydroquinoline (Aldrich), 5-chlorosulfonyl-2-oxindole and pyridine in dichloromethane was stirred at room temperature overnight. The reaction was concentrated and the residue recrystallized from methanol to vie 5-(3,4, -dihydro-2H-quinoline-1-sulfonyl)-1,3-dihydro-indol-2-one. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 10.74 (s, 1H, NH), 7.84–7.90 (d, 1H, SO2NH), 7.67–7.72 (m, 2H, 2×CH), 7.01–7.16 (m, 4H, aromatic), 6.95–6.97(d, 1H, CH), 4.28–4.29 (m, 1H), 3.58 (s, 2H, CH2), 2.59–2.65 (m, 2H), 1.75–1.77 (m, 2H), 1.53–1.61 (m, 2H). MS m/z 329 [M+1].

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-20d22dae3aee49748ffcdb0659d2075c
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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