Ethanol → Ethyl 3-ethoxyisoquinoline-4-carboxylate

HRID 64202Notes

Reaction equation

HRID 64202 reaction equation
[OH:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:17]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:18]=1.C(O)C.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:17]([O:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178470073HCID 178470073, compound

Product 1

HCID 90414090Ethyl 3-ethoxyisoquinoline-4-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the title compound of Step A (583 mg, 2.68 mmol) in THF (13 mL) was added triphenylphosphine (1.06 g, 4.03 mmol), ethanol (0.24 mL, 4.03 mmol) and DIAD (0.79 mL, 4.03 mmol). The reaction mixture was stirred at room temperature for 16 h and then the solvent was evaporated. The crude was purified via silica gel chromatography (0-30% EtOAc in hexanes) to afford the title compound of Step B (498 mg, 76%). MS (ESI) mass calcd. for C14H15NO3, 245.1. m/z found 246.1 [M+H]+. 1H NMR (500 MHz, Chloroform-d) δ 8.97 (s, 1H), 7.91-7.82 (m, 2H), 7.65-7.60 (m, 1H), 7.42-7.36 (m, 1H), 4.59-4.48 (m, 4H), 1.48-1.39 (m, 6H).

Workup

  1. customthe solvent was evaporated
  2. customThe crude was purified via silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c4b370e1b2314dbb8d2fc8aa1dec6399
Source dataset
uspto-grants-2016_09
Patent number
US09447117B2

Reaction notes

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