Hydrochloric Acid → 7-Methoxy-3-nitroquinoline

HRID 1512116Notes

Reaction equation

HRID 1512116 reaction equation
Cl.COC1C=C(N)C=CC=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([NH:19][CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=O)[CH:16]=[CH:17][CH:18]=1.C1(S)C=CC=CC=1>C(O)(=O)C>[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:16]([CH:22]=[C:21]([N+:24]([O-:26])=[O:25])[CH:20]=[N:19]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 108243-MethoxyanilineHCID 721684973-(3-Methoxy-phenylamino)-2-nitro-propenal

Product 1

HCID 6092807-Methoxy-3-nitroquinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To the HCl salt of 3-methoxy-phenylamine (4.7 g, 29.7 mmol) in 30 mL acetic acid was added 3-(3-methoxy-phenylamino)-2-nitro-propenal (3.3 g, 14.9 mmol). The reaction mixture was heated to reflux, and thiophenol (0.3 mL, 2.98 mmol) was added. After 22 h, the reaction mixture was cooled to room temperature and the solvent was removed in vacuo. Addition of 70 mL EtOAc and filtration gave solid byproduct, 7-methoxy-3-nitro-quinoline, and a filtrate, which contained impure 5-methoxy-3-nitro-quinoline. The filtrate was loaded on to silica column and eluted from 5% to 25% EtOAc in hexanes at 85 mL/min for 30 minutes. The product-enriched fractions were concentrated and taken on to the next step as a mixture of 5- and 7-methoxy substituted 3-nitroquinolines. LC/MS (m/z): 205.1 (MH+), Rt 2.26 minutes.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customthe solvent was removed in vacuo
  4. additionAddition of 70 mL EtOAc and filtration

Sources & evidence

ORD record
ord-cd49f85881064a8cb71385bce85ff581
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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