Iodoethane → 6-Chloro-3-ethoxy-5,9-diaza-benzo[c]fluoren-7-one

HRID 1840415Notes

Reaction equation

[Cl:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:28][CH3:29]>CN(C)C=O.ClCCl>[Cl:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH2:28][CH3:29])=[CH:19][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 6-chloro-3-hydroxy-5,9-diaza-benzo[c]fluoren-7-one (Example 34a) (30 mg) and potassium carbonate (60 mg) in N,N-dimethylformamide (0.5 ml) was added iodoethane (25 mg) and the mixture was stirred at 90° C. for 1.5 hrs. The reaction mixture was diluted with dichloromethane and washed with water and brine. The organic solvent was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane-methanol (100:1) to give 6-chloro-3-ethoxy-5,9-diaza-benzo[c]-fluoren-7-one (18 mg) as a yellow powder. ESI−MS: m/z 311 (MH+); 1H-NMR (CDCl3): δ1.54 (3H, t, J=7 Hz), 4.25 (2H, q, J=7 Hz), 7.39 (1H, dd, J=9 Hz, 2.5 Hz), 7.43 (1H, d, J=2.5 Hz), 8.10 (1H, d, J=5.5 Hz), 8.35 (1H, d, J=9 Hz), 8.95 (1H, d, J,=5.5 Hz), 9.04 (1H, s).

Workup

washwashed with water and brine
dry with materialThe organic solvent was dried over anhydrous sodium sulfate
customevaporated to dryness
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-1998200387f04d1d9df8a275d6a1e6b9
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680326B2

Reaction notes

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