HCID 22163750, compound → HCID 22163770, compound

HRID 1087742Notes

Reaction equation

HRID 1087742 reaction equation
[CH:1]([C:4]1[N:8]2[N:9]=[CH:10][C:11]3[C:16]([C:7]2=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]=1[CH2:23]/[CH:24]=[CH:25]/[OH:26])=[CH:15][CH:14]=[CH:13][CH:12]=3)([CH3:3])[CH3:2]>C(OCC)C.[O-2].[O-2].[Mn+4]>[CH:1]([C:4]1[N:8]2[N:9]=[CH:10][C:11]3[C:16]([C:7]2=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]=1/[CH:23]=[CH:24]/[CH:25]=[O:26])=[CH:15][CH:14]=[CH:13][CH:12]=3)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22163750HCID 22163750, compound

Product 1

HCID 22163770HCID 22163770, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of activated manganese dioxide (2.18 g) and (E)-3-(3-isopropyl-1-phenylpyrrolo[2,1-a]-phthalazin-2-yl)propen-1-ol (0.77 g) in anhydrous diethyl ether (50 ml) was stirred at the ambient temperature under an atmosphere of argon for 2 hours. The suspension was then filtered and the solid was washed thoroughly with diethyl ether (4×25 ml). The filtrate was evaporated, to give a yellow oil, which was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (5 ml; 3:1 v/v) and the solid which separated was collected, to give (E)-3-(3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazin-2-yl)propenal (0.56 g) in the form of a yellow solid, m.p. 162°-164° C. [Elemental analysis: C., 81.5; H, 6.07; N, 8.2%; calculated: C, 81.1; H, 5.92; N, 8.2%; NMR (in CDCl3): 1.6 (6H, d, J=7 Hz), 3.89 (1H, septet J=7 Hz), 5.83 (1H, dd, J=16 Hz, 8 Hz), 7.13-7.68 (10H, m), 8.29 (1H, s), 9.41 (1H, d, J=8 Hz); Mass spectrum (electron impact) m/z=340].

Workup

  1. filtrationThe suspension was then filtered
  2. washthe solid was washed thoroughly with diethyl ether (4×25 ml)
  3. customThe filtrate was evaporated
  4. customto give a yellow oil, which
  5. customwas triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (5 ml; 3:1 v/v)
  6. customthe solid which separated
  7. customwas collected

Sources & evidence

ORD record
ord-f172d6b805834583afb50906fd9a9929
Source dataset
uspto-grants-1990_10
Patent number
US04960775

Reaction notes

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