Water → 8-(3-Bromophenylamino)[1,3]dioxolo[4,5-g]quinoline-7-carbonitrile

HRID 612005Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:20])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1.Br[CH2:24]Cl.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[CH:17]=[C:16]4[O:19][CH2:24][O:20][C:15]4=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 111 °C

Procedure

A mixture of 2.17 g (6.09 mmole) of 4-[(3-bromophenyl)amino]-6,7-dihydroxy-3-quinolinecarbonitrile, 0.59 ml (1.18 g; 9.14 mmole) of bromochloromethane and 2.98 g (9.14 mmole) of cesium carbonate in 20 ml of N,N-dimethylformamide was heated and stirred for 2 hours in an oil bath at 111° C. The reaction was poured into 75 ml of water and extracted with four 50 ml portions of methylene chloride. The combined methylene chloride extracts were washed with several portions of water. This solution was taken to an oil in vacuo and this was dissolved in ethyl acetate. This solution was washed repeatedly with water, then with brine. The solution was dried over anhydrous magnesium sulfate, and taken to a solid in vacuo to give 0.95 g of 8-[(3-bromophenyl)amino]-[1,3]-dioxolo[4,5-g]quinoline-7-carbonitrile, m.p. 201-205° C.: mass spectrum (electrospray, m/e): M+H 368.1, 370.1.

Workup

temperaturewas heated
extractionextracted with four 50 ml portions of methylene chloride
washThe combined methylene chloride extracts were washed with several portions of water
dissolutionthis was dissolved in ethyl acetate
washThis solution was washed repeatedly with water
dry with materialThe solution was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record: ord-cdb09c24625442dba30f7c3bc7768128
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06002008

Reaction notes

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