1,3-Cyclopentanedione → HCID 10114142, compound

HRID 1862425Notes

Reaction equation

HRID 1862425 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[CH2:11]1[C:16](=O)[CH2:15][C:13](=[O:14])[CH2:12]1.[NH2:18][C:19]1[NH:23][N:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21](=[O:30])[CH:20]=1>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:20]3[C:21](=[O:30])[N:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[NH:23][C:19]=3[NH:18][C:16]3[CH2:11][CH2:12][C:13](=[O:14])[C:15]2=3)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

4

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 996833-Amino-1-phenyl-4,5-dihydropyrazolin-5-oneHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 10114142HCID 10114142, compoundYield 48.5%

Procedure

3-Bromo-4-fluorobenzaldehyde (0.3 g, 1.5 mmol), 1,3-cyclopentadione (0.15 g, 1.5 mmol), and 5-amino-2-phenyl-1,2-dihydropyrazol-3-one (0.26 g, 1.5 mmol) were processed as in Example 1. The resulting precipitate was chromatographed on silica gel eluting with 10% ethanol/CH2Cl2 to provide 0.32 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.26 (m, 2H), 2.63 (m, 2H), 4.86 (s, 1H), 7.21 (m, 3H), 7.4 (t, 2H), 7.51 (d, 1H), 7.67 (d, 2H),10.47 (s, 1H), 11.2 (s, 1H); MS (ESI−) m/z 438 (M+H)−; Anal. Calcd for C21H15N3FBrO2: C, 56.71;H, 3.51; N, 9.45. Found: C, 56.55;H, 3.86; N, 9.12.

Workup

  1. customThe resulting precipitate was chromatographed on silica gel eluting with 10% ethanol/CH2Cl2

Sources & evidence

ORD record
ord-5dac2f1de1ba446db46dcc7a9c414ca7
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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