Hydrochloric Acid → HCID 15067096, compound

HRID 1086253Notes

Reaction equation

HRID 1086253 reaction equation
B.[CH2:2]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][N:9]=1)[CH3:3].Cl>O1CCCC1>[CH2:2]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([CH2:12][OH:13])=[CH:10][N:9]=1)[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 15067094HCID 15067094, compound

Product 1

HCID 15067096HCID 15067096, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

40 ml of a 1M solution of borane in tetrahydrofuran are added dropwise at 0° C. to a solution of 2.11 g (10 mmol) of 6-(2-ethoxyethoxy)-nicotinic acid in 40 ml of abs. tetrahydrofuran. The mixture is stirred at room temperature for 3 hours and then acidified with concentrated hydrochloric acid, while cooling, then stirred for 30 minutes and evaporated to dryness. The residue is partitioned between ethyl acetate and saturated sodium carbonate solution, and the aqueous phase is extracted once more with ethyl acetate. The combined organic phases are washed with saturated NaCl solution, dried over sodium sulphate and evaporated. The residue crystallizes on trituration with pentane.

Workup

  1. temperaturewhile cooling
  2. stirringstirred for 30 minutes
  3. customevaporated to dryness
  4. customThe residue is partitioned between ethyl acetate and saturated sodium carbonate solution
  5. extractionthe aqueous phase is extracted once more with ethyl acetate
  6. washThe combined organic phases are washed with saturated NaCl solution
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customThe residue crystallizes on trituration with pentane

Sources & evidence

ORD record
ord-1c8eeb9f25694092a06068c2465d8d0c
Source dataset
uspto-grants-1991_07
Patent number
US05028617

Reaction notes

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