Acetic Acid → 5,6,7,8-Tetrahydroquinoline-3-carbonitrile

HRID 1626132Notes

Reaction equation

Cl[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.O.O.O.C([O-])(=O)C.[Na+].C(O)(=O)C.[OH-].[Na+]>[Zn].O>[N:3]1[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=[C:11]([C:12]#[N:13])[CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of commercially available 2-chloro-5,6,7,8-tetrahydroquinoline-3-carbonitrile [CAS no 65242-27-5] (1 g, 5.19 mmol), zinc dust (activated) (602 mg, 9.2 mmol) and sodium acetate trihydrate (694 mg, 479 μl, 5.1 mmol) in acetic acid (5.19 g, 4.95 ml, 86.4 mmol) was stirred at 60° C. for 2 hours. Water (2.5 ml) was added and the mixture stirred at 60° C. for another 5 hours. After cooling to 23° C., the mixture was basified with an aqueous solution of sodium hydroxide (1M) and filtered through Celite®. The filtrate was extracted with tetrahydrofuran, the organic layers dried over sodium sulphate and the solvent evaporated leaving a yellow liquid. The crude material was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the 5,6,7,8-tetrahydroquinoline-3-carbonitrile as a white solid (433 mg, 53% yield). MS (ISP): m/z=159.1 [M+H]+.

Workup

stirringthe mixture stirred at 60° C. for another 5 hours
temperatureAfter cooling to 23° C.
filtrationfiltered through Celite®
extractionThe filtrate was extracted with tetrahydrofuran
dry with materialthe organic layers dried over sodium sulphate
customthe solvent evaporated
customleaving a yellow liquid
customThe crude material was purified by silica gel flash chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record: ord-950be0627e4947a2b0bd54916f5250ac
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785436B2

Reaction notes

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