HCID 18659962, compound → HCID 22941953, compound

HRID 361591Notes

Reaction equation

HRID 361591 reaction equation
[N:1]1([CH2:6]/[CH:7]=[C:8](/[C:16]2[N:21]=[C:20](/[CH:22]=[CH:23]/[CH2:24][OH:25])[CH:19]=[CH:18][CH:17]=2)\[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[N:1]1([CH2:6]/[CH:7]=[C:8](/[C:16]2[N:21]=[C:20](/[CH:22]=[CH:23]/[CH:24]=[O:25])[CH:19]=[CH:18][CH:17]=2)\[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 18659962HCID 18659962, compound

Product 1

HCID 22941953HCID 22941953, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(6-[3-pyrrolidino-1-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-prop-2E-en-1-ol (1.00 g, 2.99 mmol) in DCM (20 ml) was treated portionwise with manganese dioxide (4 g, 46 mmol). The reaction mixture was stirred vigorously for 3 hours before filtration through a glass fiber pad. The filtrate was concentrated under reduced pressure to yield 3-(6-[3-pyrrolidino-1-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-prop-2E-enal as a brown solid (0.924 g, 93%). 1H-NMR; δ (CDCl3), 9.87 (1H, d, J=9.5 Hz), 7.55 (1H, t, J=7.5 Hz), 7.50 (1H, d, J=15.5 Hz), 7.33 (1H, d, J=8.0 Hz), 7.21 (2H, d, J=8.5 Hz), 7.18-7.13 (2H, m), 7.08 (2H, d, J=8.5 Hz), 6.92 (1H, d, J=9.5 Hz), 3.27 (2H, d, J=9.5 Hz), 2.62-2.27 (4H, m), 2.39 (3H, s) and 1.81-1.77 (4H, m).

Workup

  1. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1c721d67b01d41829127f06781395442
Source dataset
uspto-grants-1999_02
Patent number
US05866588

Reaction notes

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