Dimethylformamide → 2,3-Dihydro-1H-3a,6-diaza-cyclopenta[a]indene-8-carbaldehyde
Reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]1[C:10]2=[CH:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:17]=3[N:9]2[CH2:8][CH2:7]1.CN(C)[CH:20]=[O:21]>>[CH2:6]1[C:10]2=[C:11]([CH:20]=[O:21])[C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:17]=3[N:9]2[CH2:8][CH2:7]1Participants
Procedure
To dimethylformamide (0.3 ml) was added phosphorus oxychloride (0.33 ml) dropwise at 0° C. The mixture was allowed to stir for 10 min at room temperature. A solution of 2,3-dihydro-1H-3a,6-diaza-cyclopenta[a]indene (0.10 g 0.63 mMol) in 0.1 ml dimethylformamide was added and the mixture was stirred at room temperature for 3 h. The reaction was quenched with ice (ca 5 g) and the pH was adjusted to 9 by addition of 28% sodium hydroxide. The mixture was heated to reflux for 10 min. cooled to room temperature and extracted with ethyl acetate(3×5 ml) The combined organic extracts were dried with sodium sulfate and evaporated to dryness to yield the title compound (0.115 g, 97% Th). For analytical purposes a sample was recrystallised from ethyl acetate to afford slightly yellow crystals. mp 150-151° C. Found C, 70.94; H, 5.56; N, 14.97%; C11H10N2O requires C, 70.95; H, 5.41; N. 15.04%
Workup
- stirringthe mixture was stirred at room temperature for 3 h
- customThe reaction was quenched with ice (ca 5 g)
- additionthe pH was adjusted to 9 by addition of 28% sodium hydroxide
- temperatureThe mixture was heated
- temperatureto reflux for 10 min.
- temperaturecooled to room temperature
- extractionextracted with ethyl acetate(3×5 ml) The combined organic extracts
- dry with materialwere dried with sodium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-d1e34b7f7e1047dfbcff558c42bb06c8
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06583134B2
Reaction notes
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