Methanol → 2-Methoxy-5-nitroquinoline

HRID 2215387Notes

Reaction equation

HRID 2215387 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-5dc09f558bc34eac9472f4b83fd6c691
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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