Acetic Acid → N-(5-Benzyloxy-quinolin-8-yl)-benzenesulfonamide

HRID 513802Notes

Reaction equation

HRID 513802 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[CH2:23]([O:22][C:15]1[CH:14]=[CH:13][C:12]([NH:11][S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)(=[O:10])=[O:9])=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681835052-Amino-N-(5-benzyloxy-quinolin-8-yl)-benzenesulfonamide

Product 1

HCID 68183148N-(5-Benzyloxy-quinolin-8-yl)-benzenesulfonamideYield 5.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 20 general procedure 36, 2-amino-N-(5-benzyloxy-quinolin-8-yl)-benzenesulfonamide 567 (417 mg, 1.03 mmol), t-butyl nitrite (209 μl, 1.75 mmol), AcOH (4 ml) and THF (10 ml) gave the title compound (22 mg, 5%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-5f2a3fd92ce442c89a2cdcb17f9dbe96
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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