Ethyl orthoformate → HCID 67517946, compound

HRID 2173371Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[CH:8]([C:12]([O:14][CH3:15])=[O:13])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[CH:16](OCC)(OCC)OCC.[N-:26]=[N+:27]=[N-:28].[Na+]>C(O)(=O)C>[N:1]1([C:2]2[CH:11]=[CH:10][C:9]3[CH:8]([C:12]([O:14][CH3:15])=[O:13])[CH2:7][CH2:6][CH2:5][C:4]=3[N:3]=2)[CH:16]=[N:28][N:27]=[N:26]1

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 2-amino-5,6,7,8-tetrahydroquinoline-5-carboxylate (850 mg, 4.12 mmol) was stirred in acetic acid (15 ml) and tri-ethyl orthoformate (1.373 ml, 8.24 mmol) followed by sodium azide (482 mg, 7.42 mmol) then heated to 80° C. for 3 hrs. The reaction was cooled and evaporated to dryness. The mixture was taken up in DCM and washed with saturated NaHCO3 solution, then with brine. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed through a 40 g ISCO Redi-sep column and eluted with ethyl acetate:hexane (2:3) to yield methyl 2-(1H-tetrazol-1-yl)-5,6,7,8-tetrahydroquinoline-5-carboxylate. 1H-NMR (600 MHz, DMSO): δ ppm 10.07 (s, 1H), 7.92 (d, J=8.4 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H), 4.06 (t, J=5.4 Hz, 1H), 3.65 (s, 3H), 2.83-2.93 (m, 2H), 2.07-2.12 (b, 1H), 1.95-2.0 (m, 1H), 1.86-1.90 (m, 2H).

Workup

temperatureThe reaction was cooled
customevaporated to dryness
washwashed with saturated NaHCO3 solution
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated to dryness
customThe residue was chromatographed through a 40 g ISCO Redi-sep column
washeluted with ethyl acetate:hexane (2:3)

Sources & evidence

ORD record: ord-399e448e4aa04bf78851381041cd2514
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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