Hydrochloric Acid → HCID 22646652, compound

HRID 393628Notes

Reaction equation

HRID 393628 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[CH3:24])[NH2:20].Cl.C(O)C>CC(O)CC.C(O)(C)C.CCOCC>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[NH:20][C:19]1[CH:21]=[CH:22][C:23]([CH3:24])=[C:17]([OH:16])[CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 178185-Amino-2-methylphenolHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 22646652HCID 22646652, compoundYield 51.8%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolCatalystHCID 3283Diethyl EtherSolventHCID 6568(+-)-2-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 4-chloro-6,7-dimethoxyquinoline (300 mg, 1.3 mmol), (prepared as described for the starting material in Example 2), and 3-hydroxy-4-methylaniline (181 mg, 1.47 mol) in 2-butanol (13 ml) containing 5M hydrogen chloride in isopropanol (3 drops) was heated at 110° C. for 5.5 hours. Ethanol was added until the solids were completely dissolved and the solution was cooled to 0° C. Ether was added and the precipitate was collected by filtration, washed with ether and dried under vacuum to give 6,7-dimethoxy-4-(3-hydroxy-4-methylanilino)quinoline (209 mg, 46%).

Workup

  1. custom(prepared
  2. dissolutionwere completely dissolved
  3. temperaturethe solution was cooled to 0° C
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-04db9e790e2b4bac8a7d8a443941ba4e
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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