HCID 23047463, compound → HCID 23047422, compound

HRID 2107085Notes

Reaction equation

HRID 2107085 reaction equation
[CH:1]([C:4]1[N:8]2[CH: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]>[O-2].[O-2].[Mn+4].C(OCC)C>[CH:1]([C:4]1[N:8]2[CH: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 23047463HCID 23047463, compound

Product 1

HCID 23047422HCID 23047422, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of activated manganese dioxide (17.4 g), (E)-3-(3-isopropyl1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)propen-1-ol (2.14 g) and anhydrous diethyl ether (50 ml) was stirred at 20° C. under an atmosphere of argon for 17 hours. The suspension was then filtered and the filtrate was evaporated to give an orange-red oil. The oil was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v). The resulting crystalline solid was collected, washed with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v) and dried to give (E)-3-(3-isopropyl-1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)propenal (1.8 g), in the form of a yellow solid, m.p. indistinct, approximately 170° C. [N.M.R. (in CDCl3): 1.6 (6H, d, J=7 Hz), 3.76 (1H, septet, J=7 Hz), 5.72 (1H, dd, J=8 Hz and 16 Hz), 6.75 (1H, d, J=8 Hz), 7.0-7.6 (9H, m), 7.15 (1H, d, J=16 Hz), 7.82 (1H, d, J=8 Hz), 9.43 (1H, d, J=8 Hz); Mass spectrum, m/e=340 (M+H+)]

Workup

  1. filtrationThe suspension was then filtered
  2. customthe filtrate was evaporated
  3. customto give an orange-red oil
  4. customThe oil was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v)
  5. customThe resulting crystalline solid was collected
  6. washwashed with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v)
  7. customdried

Sources & evidence

ORD record
ord-e92db3a2244d4267895fe77542e7e96e
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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