Triethylamine → 2-Ethoxy-5-nitroquinoline

HRID 2182658Notes

Reaction equation

HRID 2182658 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N+:9]2[O-])([O-:3])=[O:2].C1(C)C(S(Cl)(=O)=[O:22])=CC=CC=1.C(N([CH2:31][CH3:32])CC)C>CCO>[CH2:31]([O:22][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[N:9]=1)[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 820855-Nitroquinoline 1-oxide

Product 1

HCID 219488302-Ethoxy-5-nitroquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1 g (5 mmol) of 5-nitroquinoline-1-oxide, 1.23 g (6.4 mmol) of toluenesulfonic acid chloride and 1.4 ml (9.9 mmol) of triethylamine in 30 ml of EtOH is stirred for 60 hours at room temperature. The solid is suctioned off and washed with EtOH: 870 mg of product.

Workup

  1. washwashed with EtOH

Sources & evidence

ORD record
ord-050145125b3642e1aee1253746b3246d
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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