Ethyl orthoformate → HCID 67517946, compound

HRID 2175907Notes

Reaction equation

HRID 2175907 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

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 67515804HCID 67515804, compound

Product 1

HCID 67517946HCID 67517946, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-a09505c0ce604104970e35f3cd6486f1
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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