Methanol → 2-Methoxy-5-nitroquinoline

HRID 2182653Notes

Reaction equation

HRID 2182653 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)=CC=CC=1.C(N(CC)CC)C.[CH3:33][OH:34]>>[CH3:33][O:34][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

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 820855-Nitroquinoline 1-oxide

Product 1

HCID 219488932-Methoxy-5-nitroquinoline

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 MeOH is stirred for 20 hours at room temperature. The solid is suctioned off and washed with MeOH: 565 mg of light yellow product.

Workup

  1. washwashed with MeOH

Sources & evidence

ORD record
ord-b21cb9ea2a0b430a9c9aa5f06bcb1a19
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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