Ethyl Acetate → 3-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridine

HRID 1626127Notes

Reaction equation

HRID 1626127 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]#[CH:12])=NC=1.CCCCCCC.C(OCC)(=O)C>[N+](C1C=CC=CC=1)([O-])=O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 729430295-Chloro-2-(pent-4-yn-1-yl)pyrimidine

Product 1

HCID 681078143-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A solution of 5-chloro-2-(pent-4-ynyl)pyrimidine (H. C. van der Plas, Tetrahedron 1989, 45, 5151-5162) (4.95 g (27.4 mmol) in nitrobenzene (50 ml) was heated to 210° C. for 1.5 hours under a continuous stream of nitrogen. The reaction was followed by TLC (silica gel, heptane:ethyl acetate=2:1; UV detection 254 nm). After completion, the reaction mixture was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 80:20 as the eluent. The 3-chloro-6,7-dihydro-5H-[1]pyrindine was obtained as a light brown solid (3.21 g, 76% yield). MS (ISP): m/z=154 [M+H]+.

Workup

  1. customAfter completion, the reaction mixture was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 80:20 as the eluent

Sources & evidence

ORD record
ord-50ba05c9708c4e1bba188e4c60d06330
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

Loading…