Triethylamine → 2-Ethoxy-5-nitroquinoline

HRID 2215392Notes

Reaction equation

HRID 2215392 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-286892a9ce254670b2ba47553ca2bbc0
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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