1,2,3,4-Tetrahydroquinoline → 3-(1,2,3,4-Tetrahydroquinoline-1-sulfonyl)benzoic acid

HRID 1482797Notes

Reaction equation

HRID 1482797 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[NH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1>>[N:14]1([S:2]([C:5]2[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=2)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 694601,2,3,4-TetrahydroquinolineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 23154993-(1,2,3,4-Tetrahydroquinoline-1-sulfonyl)benzoic acid

Procedure

3-(chlorosulfonyl)benzoic acid (0.5 g, 2.27 mmol) was treated with 1,2,3,4-tetrahydroquinoline (906 mg, 6.80 mmol) using method A to give 3-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzoic acid as an off white solid. Yield: 318 mg (44%). 1H-NMR: 8.17 (d, J=8.0 Hz, 1H), 8.06-8.04 (m, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.68 (t, J=8.0 Hz, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.24-7.18 (m, 1H), 7.15-7.05 (m, 2H), 3.80-3.76 (m, 2H), 2.40 (t, J=6.5 Hz, 2H), 1.61-1.54 (m, 2H).

Sources & evidence

ORD record
ord-1a5d4574d39f4c4f9b53aa925b5a5d5d
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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