Sulfuric Acid → HCID 19039886, compound

HRID 1684573Notes

Reaction equation

[NH2:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=O.[Cl:24][CH2:25][C:26]([CH2:28][Cl:29])=O.S(=O)(=O)(O)O>C(O)(=O)C>[Cl:24][C:25]1[C:26]([CH2:28][Cl:29])=[N:1][C:2]2[C:3]([C:4]=1[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=[CH:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-amino-4,5,3',4'-tetramethoxy-benzophenone (25.0 g), 1,3-dichloroacetone (11.0 g), conc. sulfuric acid (1.2 ml) and acetic acid (200 ml) was stirred at 110° C. for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was poured into water, made alkaline with 2N NaOH, and extracted with chloroform. The chloroform layer was washed with water, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (10:1, v/v) gave 3-chloro-2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (12.0 g, 38%). This compound was recrystallized from ethyl acetate-hexane to give colorless prisms, mp. 206°-207° C.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionThe residue was poured into water
extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried over magnesium sulfate
customthe solvent was evaporated under reduced pressure
washThe fractions eluted with chloroform-ethyl acetate (10:1

Sources & evidence

ORD record: ord-4d415aacc829437c8af2436e92a4b827
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05641788

Reaction notes

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