Phosphorus oxychloride → 6-chloro-9,10-methylenedioxy-7H-indeno[2,1-c]quinoline-7-on

HRID 3149Notes

Reaction equation

[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:12](=O)[C:11]=3[C:21](O)=[O:22])=[CH:4][C:3]=2[O:2]1.P(Cl)(Cl)([Cl:26])=O>O1CCCC1>[Cl:26][C:12]1[C:11]2[C:21](=[O:22])[C:6]3[C:5]([C:10]=2[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)=[CH:4][C:3]1[O:2][CH2:1][O:9][C:8]=1[CH:7]=3

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1,2-dihydro-4-(3,4-methylenedioxyphenyl)-2-oxo-3-quinoline carboxylic acid obtained in reference example 1 (10 g, 32.3 mmol) and phosphorous oxychloride (100 ml, 1.07 mol) was refluxed with heat for 4 hours. The reaction mixture was distilled to dryness and washed with n-hexane several times. To the residue obtained was added 50 g of polyphosphoric acid, and the mixture was heated at 90° C. for 2 hours. The reaction mixture was poured into ice water to filtrate a crystal precipitated. The crystal obtained was dissolved in tetrahydrofuran to filter off undissolved substances and purified by silica gel column chromatography (eluent: chloroform) to give 6.0 g (yield 59.9%) of the title compound.

Workup

temperaturewas refluxed
temperaturewith heat for 4 hours
distillationThe reaction mixture was distilled to dryness
washwashed with n-hexane several times
customTo the residue obtained
customprecipitated
customThe crystal obtained
filtrationto filter off undissolved substances
custompurified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record: ord-08a65d3d86274d87908614df5eeda1f8
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733918

Reaction notes

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